[ CAS No. 115314-14-2 ] {[proInfo.proName]}

Name: 115314-14-2|(S)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate|98%
Brand: Ambeed
SKU: A129976
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Quality Control of [ 115314-14-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 115314-14-2 ]

SDS Specification

Alternatived Products of [ 115314-14-2 ]

Product Details of [ 115314-14-2 ]

CAS No. :	115314-14-2	MDL No. :	MFCD00064582
Formula :	C₉H₉NO₆S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AIHIHVZYAAMDPM-QMMMGPOBSA-N
M.W :	259.24	Pubchem ID :	146490
Synonyms :

Calculated chemistry of [ 115314-14-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	5
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.03
TPSA :	110.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	0.73
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	-0.12
Log Po/w (SILICOS-IT) :	-0.92
Consensus Log Po/w :	0.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	3.76 mg/ml ; 0.0145 mol/l
Class :	Very soluble
Log S (Ali) :	-2.62
Solubility :	0.621 mg/ml ; 0.00239 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.91
Solubility :	3.17 mg/ml ; 0.0122 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.49

Safety of [ 115314-14-2 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P210-P201-P264-P280-P370+P378-P308+P313	UN#:	1325
Hazard Statements:	H315-H319-H341-H228	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 115314-14-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 115314-14-2 ]
Downstream synthetic route of [ 115314-14-2 ]

[ 115314-14-2 ] Synthesis Path-Upstream 1~4

1
[ 121-51-7 ]
[ 57044-25-4 ]
[ 115314-14-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	at -20℃; for 96 h;	[0251] m-Nitrobenzensulfonylchloride (12.6 g; 57 mmol) was added to a cold (-20° C.) solution of (R)-(+)-glycidol (5.5 g; 74 mmol) and TEA (10.3 mL; 74 mmol). The reaction mixture was stirred at -20° C. for 96 h. The solution was filtered and the filtrate washed with tartaric acid (10percent w/w), brine, H2O and concentrated giving the title compound in a 97percent yield. [0252] 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H)

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308[2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
[4] Patent: US2004/229900, 2004, A1, . Location in patent: Page 14
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076
[6] Patent: US5096904, 1992, A,

2
[ 121-51-7 ]
[ 60456-23-7 ]
[ 115314-14-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	at -10℃; Inert atmosphere	Reaction 1.; C₆H₄ClNO₂S C₉H₉NO₆S 221.62259.24Procedure:To a round-bottom flask 4.19 ml (S)-glycidol, 8.878 ml Of Et₃N and 150 ml of Toluene was added. The reaction mixture was stirred in a N₂ atm. The reaction80438623.1 mixture was cooled to -10⁰C. Then Nitrosulfaryl chloride was added in 3 lots. The reaction mixture was stirred for two hours. After the completion of the reaction, water was added to the reaction mixture. The compound was taken up in EtOAc. The EtOAc layer was washed with brine. The EtOAc layer was dried and concentrated. The compound was purified by column chromatography.Theoretical Yield: 16.376 g percent Yield: 93percent Yield obtained: 15.14O g 1H NMR: verified

Reference： [1] Patent: WO2010/14263, 2010, A1, . Location in patent: Page/Page column 49-50

3
[ 121-51-7 ]
[ 60456-23-7 ]
[ 115314-14-2 ]
[ 115314-14-2 ]

Reference： [1] Journal of Organic Chemistry, 1989, vol. 54, # 6, p. 1295 - 1304

4
[ 115314-14-2 ]
[ 100-51-6 ]
[ 14618-80-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3809 - 3813

[ 115314-14-2 ] Synthesis Path-Downstream 1~88

1
[ 110-91-8 ]
[ 115314-14-2 ]
[ 141395-84-8 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 1725 - 1728

2
[ 30165-97-0 ]
[ 115314-14-2 ]
[ 741719-53-9 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1295 - 1304

3
[ 112-92-5 ]
[ 115314-14-2 ]
3-O-Octadecyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

4
[ 629-96-9 ]
[ 115314-14-2 ]
3-O-Eicosyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

5
[ 143-28-2 ]
[ 115314-14-2 ]
[ 119879-72-0 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 4643 - 4648

6
[ 143-28-2 ]
[ 115314-14-2 ]
[ 119879-72-0 ]
[ 119879-81-1 ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 3077 - 3079

7
[ 2774-87-0 ]
[ 115314-14-2 ]
[ 119879-88-8 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 4643 - 4648

8
[ 2774-87-0 ]
[ 115314-14-2 ]
[ 119879-88-8 ]
[ 119879-89-9 ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 3077 - 3079

9
[ 112-72-1 ]
[ 115314-14-2 ]
3-O-Tetradecyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955
[2]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

10
[ 36653-82-4 ]
[ 115314-14-2 ]
[ 119879-73-1 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

11
[ 36653-82-4 ]
[ 115314-14-2 ]
[ 119879-73-1 ]
[ 119879-82-2 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 4643 - 4648
[2]Journal of the American Chemical Society,1989,vol. 111,p. 3077 - 3079

12
[ 7735-43-5 ]
[ 115314-14-2 ]
[ 157999-16-1 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

13
[ 7735-42-4 ]
[ 115314-14-2 ]
[ 158006-53-2 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

14
[ 90-15-3 ]
[ 115314-14-2 ]
[ 61249-00-1 ]
[ 56715-28-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1295 - 1304
[2]Journal of Organic Chemistry,1989,vol. 54,p. 1295 - 1304

15
[ 6089-04-9 ]
[ 115314-14-2 ]
[ 127705-30-0 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 5081 - 5084

16
[ 1518-84-9 ]
[ 115314-14-2 ]
[ 154531-76-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1295 - 1304

17
[ 66-56-8 ]
[ 115314-14-2 ]
[ 136116-90-0 ]
[ 142204-76-0 ]

Reference： [1]Tetrahedron Asymmetry,1992,vol. 3,p. 539 - 544

18
[ 603-85-0 ]
[ 115314-14-2 ]
[ 132059-11-1 ]
[ 132059-13-3 ]

Reference： [1]Tetrahedron Asymmetry,1992,vol. 3,p. 539 - 544

19
[ 115314-14-2 ]
[ 118629-76-8 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1295 - 1304

20
[ 31570-97-5 ]
[ 115314-14-2 ]
5-((S)-1-Oxiranylmethoxy)-1H-quinolin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 219 - 224

21
[ 115314-14-2 ]
[ 103068-41-3 ]
2-Fluoro-5-((S)-1-oxiranylmethoxy)-phenol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 219 - 224

22
[ 27688-86-4 ]
[ 115314-14-2 ]
[ 177704-09-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 539 - 548

23
[ 611-20-1 ]
[ 115314-14-2 ]
[ 93744-17-3 ]

Yield	Reaction Conditions	Operation in experiment
72%		Reaction 6.; C]9H9NO2 C9H9NO6SC7H5NO 175.18 259 24 119 12Procedure:2-Cyanophenol in acetone and K2CO3 were heated at reflux for 30 min. Then cooled Nolylate was added and heated to reflux. As in Reaction 2, the reaction was monitored by HPLC. After the completion of the reaction K2CO3 filtered/removed. The filtrate was concentrated and purified by column chromatography. 0Theoretical Yield: 10.13 g Yield Obtained: 7.3 g % Yield: 72% 1H NMR: verified

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 721 - 733
[2]Patent: WO2010/14263,2010,A1 .Location in patent: Page/Page column 55

24
[ 115314-14-2 ]
[ 765-38-8 ]
C₈H₁₅NO [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1741 - 1745

25
[ 13603-04-8 ]
[ 115314-14-2 ]
C₉H₁₇NO [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1741 - 1745

26
[ 90-15-3 ]
[ 115314-14-2 ]
[ 56715-28-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3067 - 3076

27
[ 121-51-7 ]
[ 60456-23-7 ]
[ 115314-14-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	Preparation of Compound 3; To a cooled (0 C., ice bath) solution of compound 2 (220 mg, 3.0 mmol) in anhydrous methylene chloride (10 mL) and triethylamine (1.5 mL, 10 mmol) was added 3-nitrobenzene-1-sulfonyl chloride (730 mg, 3.3 mmol) in small portions. Compound 2 is commercially available. The brown solution was allowed to stir at 0 C. for 1 h, then warmed to rt. The reaction was monitored by TLC every 15 min before all compound 2 was completely consumed. Crushed ice (1-2 g) was added to quench the reaction. The reaction mixture was transferred to a separatory funnel and partitioned between methylene chloride (20 mL) and water (10 mL). The organic layer was washed successively with saturated aqueous NaHCO3 (10 mL×3) and brine (10 mL×3), then dried over Na2SO4. After filtration and concentration, the residue was further purified by flash column chromatography to afford compound 3 as a brown solid (710 mg, 92%).1H NMR (400 MHz, CDCl3) delta 8.77 (s, 1H), 8.54 (d, J=8.1 Hz, 1H), 8.28 (d, J=7.9 Hz, 1H), 4.50 (d, J=11.5 Hz, 1H), 4.04 (dd, J=4.9 Hz, J2=1.5 Hz, 1H), 3.23 (d, J=1.8 Hz, 1H), 2.85 (dd, J1=4.0 Hz, J2=2.0 Hz, 1H), 2.64 (dd, J1=2.4 Hz, J2=2.0 Hz, 1H);13C NMR (100 MHz, CDCl3) delta 148.19, 137.92, 133.32, 130.81, 128.39, 123.16, 71.69, 48.64, 44.42.
82.8%	With triethylamine; In dichloromethane; at 0 - 5℃; for 2h;Inert atmosphere;	A 1000 ml four neck reactor was charged with DCM (250 ml, 5 v/w), 7 (50 g, 1.0 eq.). The mixture was cooled to 0±5 C and charged with TEA (102 g, 1.5 eq.).A solution of DCM (250 ml, 5 v/w) and 8 (165 g, 1.1 eq.) was added dropwise to the 1000 ml reactor at 0±5C. The reaction was stirred for 2 h and analyzed by H-NMR. The reaction mixture was filtered and the filter cake was washed with DCM (50 ml, I v/w) twice. Water (250 ml, 5 v/w) was added to the reaction and the mixture was separated. The organic phases was collected. The organic phase was washed with water (250 ml, 5 v/w). The water phases were combined and extracted with DCM (75 ml, 1 .5 v/w). The organic phase was separated and concentrated to 2-3 v. The resultant solution was charged with MTBE (250 ml, 5 v/w) and concentrated to 2-3 v twice. MTBE (400 ml, 8 v/w) was added and the mixture was stirred at 0-10C for 8 h. The reaction was filtered and the filter cake was washed with MTBE (100 ml, 2 v/w) twice. The filter cake was dried in the oven at 35- 40C for 16 h to obtain 147.3 g product as light yellow solid with purity: 98.3%, yield: 82.8%.

Reference： [1]Patent: US2009/182011,2009,A1 .Location in patent: Page/Page column 13
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 656 - 661
[3]Patent: WO2019/79540,2019,A1 .Location in patent: Paragraph 01608
[4]Tetrahedron,2009,vol. 65,p. 5984 - 5989
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2948 - 2950
[6]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4792 - 4802
[7]Journal of Medicinal Chemistry,2019,vol. 62,p. 7806 - 7839
[8]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1383 - 1387
[9]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3067 - 3076

28
[ 115314-14-2 ]
[ 135-19-3 ]
[ 129098-62-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3067 - 3076

29
[ 529-35-1 ]
[ 115314-14-2 ]
C₁₃H₁₆O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3067 - 3076

30
[ 484-17-3 ]
[ 115314-14-2 ]
C₁₇H₁₄O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3067 - 3076

31
[ 2380-94-1 ]
[ 115314-14-2 ]
[ 154632-91-4 ]

Yield	Reaction Conditions	Operation in experiment
63%		General procedure: K2CO3 (0.1433g, 1.04mmol) was added to a stirred solution of hydroxyindole (0.0461g, 0.35mmol) in dry DMF (4mL) at room temperature under argon atmosphere; after 1h a DMF solution (3mL) of compound 2 (0.0815g, 0.31mmol) was added and the mixture was stirred overnight. After 14h (TLC control, CHCl3/ CH3OH 99:1) the reaction mixture was quenched by adding ammonium chloride (saturated aqueous solution), then was extracted with diethyl ether and the organic layer washed with brine. After drying over Na2SO4, the organic layer was concentrated in vacuo and the crude was purified by column chromatography on silica gel (eluent: CH2Cl2/EtOAc 99:1). 4.2.1 (-)-(R)-4-Oxiranylmethoxy-1H-indole (3) Compound 3 was isolated as a brown thick oil (0.038 g, 63%). [alpha]D20 -6.4 (c 1.6, CHCl3); Rf 0.5 (CH2Cl2/EtOAc 99:1); deltaH (500 MHz, CDCl3) 8.25 (1H, s), 7.14-7.05 (3H, m), 6.71 (1H, t, J = 2.5 Hz), 6.55 (1H, d, J = 8.0 Hz), 4.38 (1H, dd, J = 3.0 and 11.0 Hz), 4.17 (1H, dd, J = 6.0 and 11.0 Hz), 3.49-3.47 (1H, m), 2.96 (1H, t, J = 5.0 Hz), 2.85 (1H, dd, J = 2.5 and 5.0 Hz); deltaC (125 MHz, CDCl3) 152.1, 133.2, 127.1, 120.5, 117.6, 112.3, 103.4, 102.7, 70.5, 50.9, 44.3. MS (EI) m/z: 189 (M+) (100), 132 (63), 104 (50). Anal. Calcd for C11H11NO2: C, 69.83; H, 5.86; N, 7.40. Found: C, 69.85; H, 5.84; N, 7.45.
	With sodium hydride; In N,N-dimethyl-formamide; for 3h;	EXAMPLE 39 4-Oxiranylmethoxy-1-H-indole 4-hydroxy indole (0.08 g, mmol) was dissolved in dimethylformamide (1.5 mL). Sodium hydride (0.02 g, 0.51 mmol) was slowly added to the reaction mixture followed by addition of (R)-glycidyl 3-nitrobenzene sulfonate (0.132, 0.51 mmol). A red color appeared. After 3 hour the reaction mixture was poured into a separatory funnel and ethyl acetate (100 mL) was added. The organic layer was washed 3 times with a 10% solution of sodium carbonate in water. The aqueous layers were discarded, the organic layer was dried with sodium sulfate and the solvent was removed by reduced pressure to yield crude product. The crude product was dissolved in ethyl acetate, Celite (approximately 3 grams) was added, followed by removal of the solvent under reduced pressure. The Celite/reaction mixture was loaded into an Isco solid phase loading cartridge. Flash chromatography was carried out using an Isco Companion automated chromatography system, silica column (4 g), initially holding at 5% ethyl acetate in heptane for 3 column volumes, increasing the ethyl acetate concentration to 60% over 40 column volumes, holding at 60% ethyl acetate for 10 more column volumes to yield the title compound as a residue. 1H NMR (300 Hz, CDCl3, delta) 8.17 (bs, 1H), 7.12-7.03 (m, 3H), 6.69 (d, J=2.3 Hz, 1H), 5.52 (d, 7.3 Hz, 1H), 4.35 (dd, J=3 Hz, 11 Hz, 1H), 4.15 (dd, J=5 Hz, 11 Hz, 1H), 3.45 (m, 1H), 2.93 (t, J=5 Hz, 1H), 2.81 (dd, J=3 Hz, 5 Hz, 1H) HPLC Rt=3.13 min. MS m/z [API-ES] 190.1 (M+H+).

Reference： [1]Tetrahedron,2009,vol. 65,p. 5984 - 5989
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4792 - 4802
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5600 - 5604
[4]Patent: US2008/70919,2008,A1 .Location in patent: Page/Page column 25

32
[ 115314-14-2 ]
2,3-Di-O-octadecyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

33
[ 115314-14-2 ]
2,3-Di-O-eicosyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

34
[ 115314-14-2 ]
[ 157999-06-9 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2945 - 2955

35
[ 115314-14-2 ]
[ 122470-15-9 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 4643 - 4648

36
[ 499789-57-0 ]
[ 115314-14-2 ]
[ 499789-59-2 ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was obtained according to the method of Reference Example 27 from methyl 2-(3-hydroxybenzyl)-tetrahydro-2-furancarboxylate and <strong>[115314-14-2](R)-glycidyl nosylate</strong>.1H-NMR(CDCl3): 1.62-1.72 (m, 1H), 1.76-1.86 (m, 1H), 1.88-1.95 (td, J=7.9, 13.0Hz, 1H), 2.22-2.29 (ddd, J=6.2, 9.0, 13.0Hz, 1H), 2.95 (d, J=13.9Hz, 1H), 3.18 (d,J=13.9Hz,1H), 3.69 (s, 3H), 3.85-3.97 (m, 4H), 4.15-4.22 (ddd, J=3.5, 5.1, 10.5Hz, 1H), 6.78 (d, J=7.9Hz, 1H), 6.83 (s,1H), 6.84 (d,J=7.9Hz,1H), 7.17 (t, J=7.9Hz, 1H)

Reference： [1]Patent: EP1452521,2004,A1 .Location in patent: Page 55

37
[ 392-04-1 ]
[ 115314-14-2 ]
[ 644970-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	A mixture of <strong>[392-04-1]methyl 4-fluoro-2-hydroxybenzoate</strong> (456.3 mg, 1.76 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (300 mg, 1.76 mmol) and Cs2CO3 (687.4 mg, 2.11 mmol) in DMF (4.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O, organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was opurified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit) to give the subtitled compound (385 mg). 1H-NMR (CDCl3, 400 MHz): delta 7.93-7.85 (m, 1H) ; 6.77-6.69 (m, 2H); 4.36 (dd, J = 2.6, 11.2 Hz, 1H) ; 4.08 (dd, J = 4.9, 11.2 Hz, 1H) ; 3.90 (s, 3H); 3.44 (m, 1H) ; 2.95 (m, 2H). APCI-MS: m/z 227 (MH+).

Reference： [1]Patent: WO2004/5295,2004,A1 .Location in patent: Page 143-144

38
[ 115314-14-2 ]
[ 5411-56-3 ]
[ 787585-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 2h;	(R)-1-(2-Bromophenyl)ethanol (30.0 g) and <strong>[115314-14-2](R)-glycidyl nosylate</strong>(50.3 g) were dissolved in N,N-dimethylformamide (300 ml), sodium hydride (7.76 g, 60% in oil) was added and the mixture was stirred at room temperature for 2 hr. 10% Aqueous citric acid (600 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to give the title compound (32.9 g). 1H-NMR (300MHz, deltappm, CDCl3) 7.53-7.49 (2H, m), 7.37-7.32 (1H, m), 7.16-7.10 (1H, m), 4.89 (1H, q, J=6.4Hz), 3.62-3.57 (1H, m), 3.34-3.28 (1H, m), 3.18-3.12 (1H, m), 2.79-2.76 (1H, m), 2.58-2.55 (1H, m), 1.44 (3H, d, J=6.4Hz).
	With sodium hydride; In N,N-dimethyl-formamide; oil; at 20℃; for 2h;	(1R)-(2-Bromophenyl)ethanol (30.0 g) and (R)-glycidyl 3-nitrobenzenesulfonate (50.3 g) were dissolved in dimethylformamide (300 ml) and sodium hydride (7.76 g, 60% in oil) was added. The mixture was stirred at room temperature for 2 hrs. 10% Aqueous citric acid solution (600 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to give the title compound (32.9 g). 1H-NMR (300 MHz, deltappm, CDCl3) 7.53-7.49(2H, m), 7.37-7.32(1H, m), 7.16-7.10(1H, m), 4.89(1H, q, J=6.4 Hz), 3.62-3.57(1H, m), 3.34-3.28(1H, m), 3.18-3.12(1H, m), 2.79-2.76(1H, m), 2.58-2.55(1H, m), 1.44(3H, d, J=6.4).

Reference： [1]Patent: EP1630157,2006,A1 .Location in patent: Page/Page column 45
[2]Patent: US2005/32796,2005,A1 .Location in patent: Page/Page column 39

39
[ 80311-94-0 ]
[ 115314-14-2 ]
[ 852951-41-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	A mixture of N (2-hydroxybenzyl) acetamide (382 mg, 2.31 mmol), (2S)-oxiran-2- ylmethyl-3-nitrobenzenesulfonate (599 mg, 2. 31 mmol) andCs2CO3 (901 mg, 2.77 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate andH20. The organic layer was dried overNa2S04, filtered and concentrated. The residue was purified by silica gel flash chromatography (0- 80percent ethyl acetate in petroleum spirit) to give the subtitle compound (333 mg). 1H-NMR (CDCl3, 400 MHz):8 7.32-7. 22(m, 2H); 6.95(m, 1H) ; 6.87(m, 1H); 6.34 (br. s, 1H) ; 4.55-4. 354(m, 3H); 4.03 (dd, J= 5.1, 11.2 Hz, 1H) ; 3.39(m, 1H) ; 2.95(m, 1H) ; 2.86(m, 1H) ; 1.98 (s, 3H). APCI-MS: m/z 222(mu').

Reference： [1]Patent: WO2005/49620,2005,A1 .Location in patent: Page/Page column 32

40
[ 115314-14-2 ]
2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1-oxiranylmethyl-1H-pyrazol-3-yl)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 2-CHLORO-N- (L-HYDROXY-CYCLOHEPTYLMETHYL)-5- (5-METHYL-LH- PYRAZOL-3-YL)-BENZAMIDE (3.95 g, 11 mmol), 2-tert-butylimino-2-diethylamino-1, 3- DIMETHYL-PERHYDRO-1, 2,3-diazaphosphorine on polystyrene (10.0 g, 23 mmol) in acetonitrile (60 mL) and N, N-dimethylformamide (20 mL) was stirred at room temperature for 10 minutes. 2R- (-)-GLYCIDYL 3-nitrobenzenesulfonate (3.0 g, 12.5 mmol) was added and the resulting mixture was stirred at 80 C for 8h. The mixture was filtered and concentrated in VACUO. the residue was purified by flash column chromatography (gradient dichloromethane-ethyl acetate-methanol) to afford the title compound (2. 5 g).

Reference： [1]Patent: WO2004/99146,2004,A1 .Location in patent: Page 93

41
[ 27489-33-4 ]
[ 115314-14-2 ]
[ 849465-13-0 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium carbonate; In acetone;Heating / reflux;	b) (R)-2-(2-METHANESULFONYL-PHENOXEMETHYL)-OXIRANE; To an acetone solution of the 2-sulfonylphenol described above (1.4 g, 8.14 mmol) was added (2R)- (-)-GLYCIDYL 3-nitrobenzenesulfonate (2.32 g, 8.95 mmol) and Y,, CO, (2.48 g, 17.9 mmol). The resulting mixture was stirred at reflux overnight. The reaction mixture was then cooled, filtered, and the filtrate was concentrated to give the crude product. Flash column chromatography (20% to 65% ethyl acetate/hexanes) gave 1.1 g pure product (59%).

Reference： [1]Patent: WO2005/30746,2005,A1 .Location in patent: Page/Page column 7; 15

42
[ 245057-73-2 ]
[ 115314-14-2 ]
4-(3,4-dichlorophenoxy)-1-[(2S)-oxiran-2-ylmethyl]piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In DMF (N,N-dimethyl-formamide); at 60℃;	(2No.)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate (21.1 g) in DMF (300 mL) wastreated with triethylamine (22.6 mL) followed by 4-(3,4-dichlorophenoxy)-piperidine (20g). The mixture was stirred overnight at 60C. Sodium azide (16 g) was added to the25 mixture and the reaction was stirred for a further 72 h. The solution was carefullyconcentrated under vacuum and the residue was diluted with water (600 mL), extractedwith ethyl acetate (1500 mL). The organic layer was washed twice with water (500 mL),then brine (200 mL) and concentrated under vacuum to afford an oil.

Reference： [1]Patent: WO2005/73192,2005,A1 .Location in patent: Page/Page column 23
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7702 - 7706

43
[ 246219-43-2 ]
[ 115314-14-2 ]
[ 246219-46-5 ]

Yield	Reaction Conditions	Operation in experiment
82.4%	With potassium carbonate; In acetone;	f Ethyl (R)-4-cyano-3-(oxiranylmethoxy)benzenepropionate A solution of the compound from Example 2(e) (28.3 g, 0.13 mol) and (2R)-glycidyl 3-nitrobenzenesulfonate (33.7 g, 0.13 mol) in dry acetone (500 mL) was treated with potassium carbonate (36 g, 0.26 mol) and refluxed under argon for 18 h. The reaction was cooled, filtered, and the filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (silica, 30% ethyl acetate/hexane) to yield the title compound (29.5 g, 82.4%).
82.4%	for 18h;Heating / reflux;	A solution of the compound from Example 2(e) (28.3 g, 0.13 mol) and (2R)-glycidyl 3-nitrobenzenesulfonate (33.7 g, 0.13 mol) in dry acetone (500 mL) was treated with potassium carbonate (36 g, 0.26 mol) and refluxed under argon for 18 h. The reaction was cooled, filtered, and the filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (silica, 30% ethyl acetate/hexane) to yield the title compound (29.5 g, 82.4%).

Reference： [1]Patent: US2003/18203,2003,A1
[2]Patent: US2004/14723,2004,A1 .Location in patent: Page/Page column 7

44
[ 288067-36-7 ]
[ 115314-14-2 ]
[ 288067-37-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In acetone; for 24h;Heating / reflux;	A mixture of Example 5(b) (0.71 g, 2.7 mmol), potassium carbonate (0.73 g, 5.3 mmol), and R-glycidyl-3-nitrobenzenesulfonate (0.73 g, 2.8 mmol) in acetone (30 mL) was heated at relux in 24 h. The mixture was cooled, concentrated, taken up in H2O, extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, concentrated to afford the above titled compound as an off white solid (0.7 g, 82%). NMR (300 Mz DMSO-d6): delta 1.32(t, J=7.1 Hz,3H), 2.78(dd, J=2.6, 4.9 Hz, 1H), 2.91(t, J=4.9, 1H), 3.44(m, 1H), 4.20(dd, J=6.5, 11.7, 1H), 4.39(q, J=7.1 Hz, 2H), 4.72(dd, J=2.6, 11.7 Hz, 1H), 7.47(dd, J=1.4, 8 Hz, 1H), 7.57(d, J=1.4 Hz, 1H), 7.85(d, J=8 Hz, 1H), 7.95(d, J=8.5 Hz, 1H), 8.08(d, J=8.5 Hz, 1H).

Reference： [1]Patent: US2004/14723,2004,A1 .Location in patent: Page/Page column 8

45
3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-[(4-hydroxyphenyl)methyl]-5-isopropyl-1H-pyrazole [ No CAS ]
[ 115314-14-2 ]
3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[(R)-2,3-epoxypropoxy]phenyl}methyl)-5-isopropyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 24h;	Example 533-(beta-D-Glucopyranosyloxy)-4-[(4-{(R)-2-hydroxy-3-[2-hydroxy-1-(hydroxymethyl)-1-(methyl)ethylamino]propoxy}-phenyl)methyl]-5-isopropyl-1H-pyrazole A mixture of 3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-hydroxyphenyl)methyl]-5-isopropyl-1H-pyrazole (0.55 g), (R)-1-(3-nitrobenzenesulfonyloxy)-2,3-epoxypropane (0.38 g) and cesium carbonate (0.57 g) inN,N-dimethylformamide (5 mL) was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 2/1) to give 3-(2,3,4,6- tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-({4-[(R)-2,3-epoxypropoxy]phenyl}methyl)-5-isopropyl-1H-pyrazole (0.4 g). This material (43 mg) was dissolved in ethanol (1.5 mL). To the solution was added 2-amino-2-methyl-1,3-propanediol (51 mg), and the mixture was stirred at 75 C for 14 hours. To the reaction mixture was added 1 mol/L aqueous sodium hydroxide solution (0.28 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was directly purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 mum, 120 A, 20 x 50 mm, flow rate 30 mL/minute linear gradient, water/methanol = 90/10 - 10/90) to give the title compound (12 mg).1HNMR (CD3OD) delta ppm: 1.0 (3H, s), 1.05-1.15 (6H, m), 2.68 (1H, dd, J=11.6Hz, 8.1Hz), 2.78 (1H, dd, J=11.6Hz, 3.8Hz), 2.8-2.95 (1H, m), 3.25-3.55 (8H, m), 3.6-3.7 (2H, m), 3.73 (1H, d, J=16.1Hz), 3.8-4.0 (4H, m), 5.0-5.1 (1H, m), 6.75-6.85 (2H, m), 7.05-7.15 (2H, m)

Reference： [1]Patent: EP1548024,2005,A1 .Location in patent: Page/Page column 64

46
3-(6-cyano-5-hydroxy-pyridin-2-yl)-propionic acid ethyl ester hydrochloride [ No CAS ]
[ 115314-14-2 ]
3-[6-Cyano-5-((R)-1-oxiranylmethoxy)-pyridin-2-yl]-propionic Acid Ethyl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 18h;Heating / reflux;	A solution of a one-to-one mixture of the compound from Example 1(f) and (2R)-glycidyl 3-nitrobenzenesulfonate in dry acetone is treated with potassium carbonate (3 equivalents) and heated at reflux under argon for 18 h. The reaction is cooled, filtered, and the filtrate is concentrated in vacuo and the residue is purified by flash column chromatography to give the above titled compound.

Reference： [1]Patent: US2004/9980,2004,A1 .Location in patent: Page/Page column 7

47
[ 115314-14-2 ]
[ 186590-23-8 ]
[ 862992-87-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In acetone; for 24h;Heating / reflux;	A solution of 6- Bromo-2,3-difluoro phenol from Example la (2.0 g, 9.47 moles) and (2R) -glycidyl 3- nitrobenzenesulfonate (2.45 g, 9.47 moles) ) in dry acetone (500 mL) was treated with potassium carbonate (3.93 g, 28.41 moles) and refluxed under nitrogen for 24 h. The reaction was cooled, filtered and filtrate was concentrated in vacuo and the residue was flash column chromatographed (25% ethyl acetate/hexanes) to yield the desired product (2.19 g) in 87% yield.'H-NMR (400 MHz, CDCl3) 0 0 7. 5 5 (dd, J=2.6, 4.1 Hz, 1H), 7.30-7. 26 (m, 1H), 6.90-6. 83 (m, 1H), 4.40-4. 36 (m, 1H), 4.15-4. 10 (m, 1H), 3.44-3. 40 (m, 1H), 2.91-2. 88 (m, 1H), 2.75-2. 73 (m, 1H).

Reference： [1]Patent: WO2005/77892,2005,A1 .Location in patent: Page/Page column 15

48
[ 110894-91-2 ]
[ 115314-14-2 ]
[ 330651-27-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydride; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 1.33333h;	Add a solution of 3-thieno[2,3-d]isoxazol-3-yl-phenol (Example 1, 1.36 g, 0.0063 mol) and dry dimethylformamide (14 mL) to a stirred suspension of sodium hydride (0.27 g, 0.0068 mol, 60% in oil) and dry dimethylformamide (14 mL). Cool the mixture to 0C and add dropwise a solution of <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (1.61 g, 0.0062 mol, recrystallized twice from absolute ethanol) and dimethylformamide (14 mL). Stir at 0C for 0.5 hour, warm to room temperature over 40 min., and stir at room temperature for 10 min. Pour the mixture into ice/ammonium chloride; extract with ether; wash the extract with cold 0.5N NaOH solution and brine; dry (Na2SO4); filter, and concentrate to afford a white solid. Purify the solid by flash chromatography on silica gel by dissolving in ethyl acetate, applying to the column and eluting with 25% ethyl acetate in heptane to afford the title compound as a white solid (1.15 g, 68% yield), >98% ee by chiral HPLC (Chiralcel OD column, 0.75 mL/min, 90% heptane/10% isopropyl alcohol, UV detector (237 nm). The material may be recrystallized from absolute ethanol.
	With potassium tert-butylate; In 1-methyl-pyrrolidin-2-one; at 0 - 5℃; for 4.5h;	Add potassium t-butoxide (1.12 g, 0.010 mol) to a stirred, chilled (10C) solution of 3-thieno[2,3-d]isoxazol-3-yl-phenol (Example 1, 2.17 g, 0.010 mol) and N-methylpyrrolidinone (30 mL). After 0.5 hour, cool the mixture to 0-5C and add <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (2.59 g, 0.010 mol, 99%ee, Aldrich Chemical Company). After 2 hours, add potassium t-butoxide (0.2 equiv.) and <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (0.1 equiv.), and stir for 2 hours at which time the reaction is 96% complete [monitor the reaction by HPLC [Waters mu-Bondpack C-18 column, 0.1N ammonium formate/acetonitrile (40:60), flow rate 1 mUmin., UV detection at 240 nm]. Treat the solution of (R)-3-(3-epoxymethoxyphenyl)thieno[2,3-d]isoxazole with 1-(2-methoxyphenyl)piperazine (5.80 g, 0.030 mol, Aldrich Chemical Company) and heat to 70C for six hours. Cool the reaction mixture to 23C, pour into water (300 mL) and extract with ethyl acetate (1x300 mL, 2x100mL). Wash the combined extracts with 5% sodium chloride solution (3.50mL), dry (K2CO3), filter and concentrate in vacuo. Purify the material twice by elution through silica gel with ethyl acetate to give the free base of the title compound, 4.15 g (89% yield). Convert to the hydrochloride salt by treating an absolute ethanol (20 mL) solution of the free base with 37% hydrochloric acid solution (0.74 mL) at 25C. Concentrate the slurry to 10 mL final volume, chill to -20C for 0.5 hour, isolate and dry (90C, 4 hours) the filter cake to afford the title compound, 3.55 g (79% yield), m.p. 179-181 C, >98% ee by chiral HPLC, MS (chemical ionization, CH4), MH+ 466; NMR (DMSO-d6) and IR (KBr) consistent with the structure of the title compound. Analysis: Calculated for C25H27N3O4S·HCl : 59.81%C, 5.62%H, 8.37%N; Found: 59.53%C, 5.51 %H, 8.18%N

Reference： [1]Patent: EP1216250,2003,B1 .Location in patent: Page/Page column 27
[2]Patent: EP1216250,2003,B1 .Location in patent: Page/Page column 32; 33; 54; 56; 57

49
[ 115314-14-2 ]
[ 908248-26-0 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 57; Preparation of (S)-(3,4-dihydro-7-nitro-2H-benzo[b][1,4]oxazin-3-yl)methanol; (S)-(3,4-dihydro-7-nitro-2H-benzo[b][1,4]oxazin-3-yl)methanol Sodium hydride (0.810 g, 0.0202 mol) was added slowly to a mixture of 2-amino-5-nitrophenol (3.0 g, 0.019 mol) in dmf (50 ml) at 0 C. The mixture was stirred at rt for 1 h and then (r)-(oxiran-2-yl)methyl 3-nitrobenzenesulfonate (5.0 g, 0.019 mol) was added. The mixture was stirred at room temperature overnight and then DMF was removed under vacuum. The residue was partitioned between water and EtOAc. The organic layer was washed with aqueous Na2CO3 solution, brine, dried (Na2SO4) and concentrated under vacuum to give a brown solid (5.2 g). A mixture of the above brown solid, K2CO3 (2.0 g) and DMF (200 ml) was stirred at 120 C. under N2 overnight. After cooling, the solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography on silica gel with CH2Cl2-EtOAc (containing 5% Et3N-0 to 60%) to give the product as a soft brown solid. LC-MS: 2.30 min, 211.1 (m+1).

Reference： [1]Patent: US2006/194801,2006,A1 .Location in patent: Page/Page column 54

50
[ 115314-14-2 ]
[ 224450-46-8 ]
[ 224449-82-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 13 Synthesis of (2R)-1-[(4-tert-butoxycarbonylamino-2,3,5-trimethyl)phenoxy]-2,3-epoxypropane (19) The same procedure was followed as in Example 3 using (4-tert-butoxycarbonylamino-2,3,5-trimethyl)phenol and (R)-glycidyl 3-nitrobenzenesulfonate to produce the above.

Reference： [1]Patent: US6407099,2002,B1

51
[ 115314-14-2 ]
[ 224450-48-0 ]
[ 224449-83-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 14 Synthesis of (2R)-1-[(5-tert-butoxycarbonylamino-2-methoxy)phenoxy]-2,3-epoxypropane 20) The same procedure was followed as in Example 3 using (5-tert-butoxycarbonylamino-2-methoxy)phenol and (R)-glycidyl 3-nitrobenzenesulfonate to produce the above.

Reference： [1]Patent: US6407099,2002,B1

52
[ 81382-45-8 ]
[ 115314-14-2 ]
[ 340784-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethyl acetate; acetone;	EXAMPLE 2 Preparation of (S)-3-(Indazol-4-yloxy)-1,2-Epoxypropane Potassium carbonate (6.8 grams, 0.05 moles) was added to <strong>[81382-45-8]4-hydroxyindazole</strong> (3.3 grams, 0.025 moles), and (2S)-(+)-glycidyl 3-nitrobenzenesulfonate (6.5 grams, 0.025 moles) in acetone at room temperature. The reaction was heated to reflux for 3 hours. TLC (50% ethyl acetate/hexane) indicated that while little starting material was left, a bright-UV product spot appeared in between the starting materials. The reaction was filtered and concentrated to a dark green oil. The oil-was dissolved in ethyl acetate and partitioned with water three times. The organic was dried with magnesium sulfate, filtered, and concentrated to a green oil. The oil was filtered over a silica pad with a 40% ethyl acetate/hexane mixture, resulting in a light green oil (4.1 grams, 88%). The product is unstable when left at room temperature or in solution for long periods of time and is usually stored in the freezer or used immediately in the epoxide opening reaction. Yield: 50-80%. NMR was consistent with the formation of the desired product.

Reference： [1]Patent: US6534504,2003,B1

53
[ 214623-86-6 ]
[ 584-08-7 ]
[ 115314-14-2 ]
[2,3-Dichloro-4-(N,N-dipropylsulfamoyl)]phenyl glycidyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethyl acetate; acetone;	d) [2,3-Dichloro-4-(N,N-dipropylsulfamoyl)]phenyl glycidyl ether. The compound of Example 86c (5.0 g, 15.3 mmol), K2 CO3 (6.4 g, 46.0 mmol), and (2R)-(-)-glycidyl 3-nitrobenzene-sulfonate (5.6 g, 15.3 mmol) were heated in acetone (250 mL) to reflux 18 hours. The solvent was concentrated in vacuo to half volume, poured into H2 O, extracted with EtOAc, the combined organic extracts were dried (MgSO4), evaporated and purified by column chromatography (silica gel, 40% EtOAc in hexanes) to give the title compound as a clear oil (4.9 g, 84%). 1H NMR (400 MHz, CDCl3) d 8.04 (d, J=8 Hz, 1H), 6.94 (d, J=8 Hz, 1H), 4.45 (dd, J=1, 9 Hz, 1H), 4.11 (dd, J=7, 11 Hz, 1H), 3.44 (m, 1H), 3.24 (t, J=9, 18 Hz, 4H), 2.97 (m,1H), 2.87(m, 1H), 1.52 (m, 4H), 0.84 (t, J=6,14 Hz, 6H)

Reference： [1]Patent: US6022894,2000,A

54
[ 611-20-1 ]
[ 115314-14-2 ]
[ 38465-16-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 73: Preparation of (R)-N-[2-Hydroxy-3-(2-cyanophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride, Compound 122 STR73 Using the method of Example 60, supra, 2-cyanophenol (0.54 g, 4.5 mmol), sodium hydride (0.188 g, 4.7 mmol), and <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (1.06 g, 4.1 mmol) were used to prepare 350 mg of (R)-2-cyanophenyl glycidyl ether.

Reference： [1]Patent: US6022894,2000,A

55
[ 115314-14-2 ]
[ 108-95-2 ]
(R)-2,3-epoxyphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With cesium fluoride; In water; N,N-dimethyl-formamide;	EXAMPLE 2 Phenol (1.09 g) was dissolved in DMF (5 ml) under nitrogen atmosphere and the solution was cooled to 0 C. Cesium fluoride (2.29 g) was added thereto, and the mixture was stirred for 1 hour. Then, R-glycidyl m-nitrobenzenesulfonate (3.0 g, 99.3% e.e.) was added thereto and the mixture was stirred for 12 hours at the same temperature. After the reaction, water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 50:1) to give 1.55 g of (R)-2,3-epoxyphenol (yield 89%, optical purity 98.5% e.e.) as a colorless oil. [alpha]D (21 C., c=2.86, CH3 OH)=-15.1 NMR(CDCl3) delta:2.76(1H, m), 2.90(1H, m), 3.30-3.45(1H, m), 3.96(1H, dd), 4.21(1H, m), 6.85-7.09(3H, m), 7.21-7.41(2H, m)

Reference： [1]Patent: US6087512,2000,A

56
1-fluoro-4-hydroxycarbazole [ No CAS ]
[ 115314-14-2 ]
O-Glycidyl-1-Fluoro-4-Hydroxycarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; In acetone;	Preparation 122 O-Glycidyl-1-Fluoro-4-Hydroxycarbazole STR141 A mixture of 1-fluoro-4-hydroxycarbazole (470 mg, 2 mmol), potassium carbonate (345 mg, 2.5 mmol), <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong>, (518 mg, 2 mmol), and 20 mL of acetone was heated to reflux for about 18 hours. The reaction was cooled and concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via flash silica gel chromatography eluding with 10% ethyl acetate/hexanes to give 247 mg of the title compound. Yield: 48%. 1 H NMR. MS(FD)

Reference： [1]Patent: US6140352,2000,A

57
[ 14300-33-5 ]
[ 115314-14-2 ]
[ 804555-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; at 0 - 20℃; for 5h;	Step 2 (2R)-2-[(dicyclopropylmethoxy)methyl]oxirane Dicyclopropylmethanol (880 mg) obtained in Step 1 and <strong>[115314-14-2](R)-glycidyl nosylate</strong> (3.05 g) were dissolved in tetrahydrofuran (7.3 ml), sodium hydride (471 mg) and dimethyl sulfoxide (1.5 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 5 hr. Water was poured into the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10) to give the title compound (760 mg).

Reference： [1]Patent: EP1630157,2006,A1 .Location in patent: Page/Page column 49

58
[ 122752-70-9 ]
[ 115314-14-2 ]
[ 804555-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; at 0 - 20℃;	Step 1 (R)-2-[[1-(2-iodophenyl)ethoxy]methyl]oxirane 2-Iodoacetophenone (6.30 g) was dissolved in methanol (50 ml), sodium borohydride (726 mg) was added and the mixture was stirred at room temperature for 1.5 hr. 10% Aqueous citric acid was added to the reaction mixture and ethanol was evaporated. Water was added and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was dissolved in tetrahydrofuran (50 ml). The solution was cooled to 0C, sodium hydride (1.54 g, 60% in oil), <strong>[115314-14-2](R)-glycidyl nosylate</strong> (9.95 g) and dimethyl sulfoxide (10 ml) were successively added, and the mixture was stirred overnight at 0C - room temperature. 10% Aqueous citric acid was added to neutralize the reaction mixture, and extracted 3 times with ethyl acetate. The organic layer was washed successively with water (twice) and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (6.36 g).

Reference： [1]Patent: EP1630157,2006,A1 .Location in patent: Page/Page column 58-59

Yield	Reaction Conditions	Operation in experiment
7.4 g (70%)		EXAMPLE B (2R)-(-)-Glycidyl-3-nitrobenzenesulfonate The procedure of Example A was repeated with S-glycidol (3.0 g, 40.5 mmol) (Arco Chemical Company, Newton Square, Pa.) in place of R-glycidol to provide 7.4 g (70%) of (2R)-(-)-glycidyl-3-nitrobenzenesulfonate, m.p.=61-63 C., [alpha]D -21.5(c0.97, chloroform)
		Examples of sulfonic acid esters useful in the tertiary amine combinatorial process of this invention are the following: Sulfonic Acid Esters -- ... (2r)-(-)-glycidyl tosylate (s)-(+)-2-methylbutyl methanesulfonate (s)-(+)-2-methylbutyl p-toluenesulfonate (s)-(+)-1-phenyl-1,2-ethanediol 2-tosylate (2r)-(-)-glycidyl 3-nitrobenzenesulfonate propargyl benzenesulfonate 2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (r)-(-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate ...

60
[ 115314-14-2 ]
(2S)-(-)-glycidyl-2-cyanobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.3 g (85%)		EXAMPLE D (2S)-(-)-Glycidyl-2-cyanobenzene The procedure of Example C was repeated with 4.0 g (15.4 mmol) of 2R-(-)-glycidyl-3-nitrobnezenesulfonate from Example B in place of the (2S) isomer to provide 2.3 g (85%) of (2S)-(-)-glycidyl-2-cyanobenzene as a crystalline solid, m.p. 88-89 C., [alpha]D -24.4(c 1.82, methanol).

Reference： [1]Patent: US5096904,1992,A

61
[ 1006-50-4 ]
[ 115314-14-2 ]
(S)-5-(glycidyl)-thioquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen sulfide; tert.-butyl lithium; In tetrahydrofuran; hexane;	Example 2a (S)-5-(glycidyl)-thioquinoline To a solution of 0.13 g (0.51 mmol) of 5-iodoquinoline in 4 ml of tetrahydrofuran at -78C was added 0.59 ml (1.0 mmol) of tert-butyllithium (1.7M in hexane). After 10 minutes, 20 mg (0.61 mmol) of sulfur were added and the cooling was removed. After 40 minutes, the reaction was cooled to 5C and 0.132 g (0.51 mmol) of <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> was added. After 30 minutes, the reaction was poured into cold brine, extracted with ethyl acetate, and concentrated under reduced pressure to an orange residue. The residue was chromatographed on a silica gel column and eluted with 2% methanol-dichloromethane to obtain 27 mg of (S)-5-(glycidyl)-thioquinoline. 1H-NMR (CDCl3, 300 MHz) delta 2.41 (m, 1H); 2.72 (m, 1H,); 3.02 (t, 1H, J = 4.4Hz); 3.16 (m, 2H); 7.45 (dd, 1H, J = 8.5 and 4.2 Hz); 7.65 (m, 2H); 8.05 (d, 1H, J = 8.0 Hz); 8.8 (d, 1H, J = 8.7Hz); 8.93 (m, 1H). Mass spec. m/e = 217 = p.

Reference： [1]Patent: EP844244,1998,A1

62
[ 115314-14-2 ]
[ 57260-71-6 ]
[ 159873-06-0 ]

Yield	Reaction Conditions	Operation in experiment
70%		(S)-4-Oxiranylmethyl-piperazine-1-carboxylic acidtert-butyl ester The same method as employed in the preparation of Intermediate 1 but starting from piperazine-1-carboxylic acid tert-butyl ester and <strong>[115314-14-2](R)-(-)-3-nitro-benzenesulfonic acid oxiranylmethyl ester</strong> gave after flash chromatography the title compound as a yellow oil in a 70% yield. 1H NMR (CDCl3,300 MHz) delta 3.42 (m, 3H), 3.08 (m, 1H), 2.76 (m, 2H), 2.57-2.45 (m, 6H), 2.25 (dd, 1H, J= 13.3, 6.9 Hz), 1.44 (s, 9H).

Reference： [1]Patent: EP1094063,2001,A1

63
[ 65540-09-2 ]
[ 115314-14-2 ]
2-(4-benzo[b]thiophen-3-yl-phenoxymethyl)-oxirane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In N-methyl-acetamide; water; mineral oil;	Scheme III, Step N: Cool a mixture of sodium hydride (585 mg, 60% dispersion in mineral oil, 14.6 mmol) in dimethylformamide (20 mL, anhydrous), with an ice bath, under a nitrogen atmosphere. Add a solution of 4-benzo[b]thiophen-3-yl-phenol (3.0 g, 13.3 mmol) in dimethylformamide (20 mL) over a period of 5 minutes. Reaction mixture has noticeable gas evolution and is a yellow mixture. Stir at room temperature for 0.5 hours and cool via an ice bath to give a yellow solution. Rapidly, add a solution of <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (3.78 g, 14.6 mmol) in dimethylformamide (20 mL) and stir at 0C for 35 minutes. The reaction mixture is a red-orange color. Stir reaction mixture at room temperature overnight. Pour the reaction mixture into cold (0C) water (300 mL) and extract with ethyl acetate (3x100 mL). Combine the organic layers, wash with water (100 mL), saturated sodium chloride (100 mL), dry (MgSO4) and concentrate (in vacuo) to give a brown oil. The brown oil is purified by column chromatography (dichloromethane) to give a light green/clear, viscous oil. The oil is dried (0.5 mm Hg) at room temperature for 3 hours to give the title compound as a solid (3.19 g, 85% Yield).

Reference： [1]Patent: EP1216244,2003,B1

64
2-cyano-4-(N,N-dipropylaminocarbonyl)phenol [ No CAS ]
[ 115314-14-2 ]
[ 214623-77-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone;	c) Preparation of [2-cyano-4-(N,N-dipropylaminocarbonyl)]phenyl R-glycidyl ether The compound of example 10(b) (470 mg, 2.04 mmol), K2CO3 (563 mg, 4.08 mmol), and (2R)-(-)-glycidyl-3-nitrobenzenesulfonate (528 mg, 2.04 mmol) were heated in acetone (30 mL) at reflux for 18 h. The solvent was concentrated in vacuo to half of the volume, poured into H2O and extracted with EtOAc. The combined organic extracts were dried (MgSO4), evaporated and the residue purified by column chromatography (silica gel, 80% EtOAc/hexanes) to give the title compound as a clear oil. 1H NMR (CDCl3, 250 MHz) d 7.6-7.3 (2H, m), 7.02 (1H, d), 4.47-4.41 (1H, d of d), 4.13-4.08 (1H, m) 3.4-3.2 (5H, m), 2.86-2.83 (2H, m) 1.6 (4H, br s), 0.9-0.8 (6H, m).

Reference： [1]Patent: US6294531,2001,B1

65
[ 214623-86-6 ]
[ 115314-14-2 ]
[2,3-Dichloro-4-(N,N-dipropylsulfamoyl)]phenyl glycidyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; In acetone;	d [2,3-dichloro-4-(N,N-dipropylsulfamoyl)]phenyl glycidyl ether The compound of Example 15(c) (5.0 g, 15.3 mmol), K2CO3 (6.4 g, 46.0 mmol), and <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (5.6 g, 15.3 mmol) were heated in acetone (250 mL) to reflux 18 h. The solvent was concentrated in vacuo to half volume, poured into H2O, extracted with EtOAc, the combined organic extracts were dried over MgSO4, evaporated and purified by column chromatography (silica gel, 40% EtOAc/Hexanes) to give the title compound as a clear oil (4.9 g, 84%). 1H NMR (400 MHz, CDCl3) d 8.04 (d, J=8 Hz, 1H), 6.94 (d, J=8 Hz, 1H), 4.45 (dd, J=1,9 Hz, 1H), 4.11 (dd, J=7,11 Hz, 1H), 3.44 (m, 1H), 3.24 (t, J=9,18 Hz, 4H), 2.97 (m, 1H), 2.87(m, 1H), 1.52 (m, 4H), 0.84 (t, J=6,14 Hz, 6H).

Reference： [1]Patent: US6294531,2001,B1

66
[ 115314-14-2 ]
[ 71031-03-3 ]

Yield	Reaction Conditions	Operation in experiment
81.1%		(R)-2-phenoxymethyl-oxirane Add phenol (1.089 g, 11.572 mmol) to a slurry of sodium hydride (0.347 g, 14.465 mmol) in N,N-dimethylformamide (77.1 mL) and stir at room temperature for 40 minutes. Add 3-nitrobenzenesulfonic acid (R)-1-oxiranylmethyl ester (3.00 g, 11.572 mmol) and stir at room temperature for 16 hours (J. Org. Chem., 54, 1296-1304 (1989). Quench with saturated aqueous ammonium chloride (75 mL), dilute with water (75 mL) and extract with diethyl ether (3*300 mL). Combine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL), dry (magnesium sulfate), filter and purify (silica gel chromatography, eluding with 10:90 to 50:50 ethyl acetate:hexanes) to give the desired compound as a clear liquid (1.410 g, 81.1%). GC-MS=150 [M]

Reference： [1]Patent: US2007/225267,2007,A1 .Location in patent: Page/Page column 43

67
[ 674475-88-8 ]
[ 115314-14-2 ]
[ 674476-05-2 ]

Yield	Reaction Conditions	Operation in experiment
		1 -(4-Fluoro-phenyl)-8-(8-methyl-naphthalen-1 -ylmethyl)-1 ,3,8-triaza- spiro[4.5]-decan-4-one (2.0 g, 4.95 mmol) was dissolved in N, N- dimethylfornnannide (25.0 ml_). To the reaction mixture was then added at O0C sodium hydride (60% in mineral oil, 238 mg, 5.94 mmol) under nitrogen atmosphere and the reaction mixture was stirred at O0C for one hour. To the reaction mixture was then added at O0C (2R)-(-)-glycidyl-3- nitrobenzenesulfonate (1.54 g, 5.94 mmol). The reaction mixture was stirred at O0C for one hour, then at room temperature under nitrogen atmosphere for 18 hours and partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (2.5% methanol/dichloromethane) to yield the title compound as a foam.1H NMR (300 MHz, CDCI3) £7.78-7.76 (1 H, m), 7.73-7.69 (1 H, m), 7.38- 7.31 (4H, m), 6.99-6.91 (2H, m), 6.89-6.84 (2H, m), 4.76 (1 H, d, J = 4.8 Hz), 4.65 (1 H, d, J = 4.8 Hz), 4.01 (2H, s), 3.20-3.11 (6H, m), 2.86-2.77 (5H, m), 2.61 -2.59 (1 H, m), 2.31 -2.21 (2H, m), 1.69-1.63 (2H, m)MS (ES+) m/z 460.2 (M + H)+.
		[1- (4-FLUORO-PHENYI)-8- (8-METHYL-NAPHTHALEN-1-YLMETHYL)-1,] 3,8-triaza- spiro [4. [5]-DECAN-4-ONE] (2.0 g, 4.95 [MMOL)] was dissolved in N, N- [DIMETHYLFORMAMIDE] (25.0 mL). To the reaction mixture was then added at [0C] sodium hydride [(60%] in mineral oil, 238 mg, 5.94 mmol) under nitrogen atmosphere and the reaction mixture was stirred at [0C] for one hour. To the reaction mixture was then added at [0C] (2R)- (-)-glycidyl-3- nitrobenzenesulfonate (1.54 g, 5.94 [MMOL).] The reaction mixture was stirred at [0C] for one hour, then at room temperature under nitrogen atmosphere for 18 hours and partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with [NA2SO4,] filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (2.5% [METHANOL/DICHLOROMETHANE)] to yield the title compound as a foam. 'H NMR (300 MHz, [CDCI3)] [67.] 78-7.76 (1 H, m), 7.73-7. 69 [(1 H, M),] 7.38- 7.31 (4H, m), 6.99-6. 91 (2H, m), 6.89-6. 84 (2H, m), 4.76 (1 H, d, J = 4.8 Hz), 4.65 (1 H, d, J = 4.8 Hz), 4.01 (2H, s), 3.20-3. 11 (6H, m), 2.86-2. 77 (5H, m), 2.61-2. 59 [(1H, M),] 2.31-2. 21 (2H, m), 1.69-1. 63 (2H, m) MS [(ES+)] m/z 460.2 [(M] + H) +.

Reference： [1]Patent: WO2008/67177,2008,A2 .Location in patent: Page/Page column 20
[2]Patent: WO2004/22558,2004,A2 .Location in patent: Page 159-160

68
[ 115314-14-2 ]
[ 140675-43-0 ]
[ 1037411-85-0 ]

Yield	Reaction Conditions	Operation in experiment
82%		CsF (2.80 g, 18.17 mmol) was added to a solution of 2-fluoro-6- hydroxybenzonitrile (0.83 g, 6.06 mmol) dissolved in anhydrous DMF (4.0 mL). The resulting suspension stirred at room temperature for 2 hours, before the addition of (25)-(+)-glycidol nosylate (1.57 g, 6.06 mmol). After completion of addition the reaction continued to stir at room temperature overnight. The next day, the reaction mixture was diluted with water and a white precipitate formed. The white solid was collected via filtration and washed with water to afford the title compound (0.96 g, 82%) in good yield. 1H NMR (DMSO-Cl6, 300 MHz): delta 7.77-7.68 (m, IH), 7.14- 7.06 (m, 2H), 4.59 (dd, J= 3.0, 12.0 Hz, IH), 4.08 (dd, J= 6.0, 9.0 Hz, IH), 3.39 (m, IH), 2.88 (t, J= 6.0 Hz, IH), 2.76 (dd, J= 3.0, 6.0 Hz, IH).

Reference： [1]Patent: WO2008/83054,2008,A2 .Location in patent: Page/Page column 33

69
[ 877457-71-1 ]
[ 115314-14-2 ]
[ 1075260-31-9 ]

Yield	Reaction Conditions	Operation in experiment
85%		Example 72; 10-Chloro-3-({4- [(2,3-dihydro [ 1 ,4] dioxino [2,3-c] pyridin-7- ylmethyl)amino] -1-piperidinyl} methyl)-2,3-dihydro-5H- [1,4] oxazino [4,3,2- flfe]quinoxalin-5-one dihydrochloride (Enantiomer 2); (a ) 7-Chloro-2-(methyloxy)-8- { [(2i?)-2-oxiranylmethyl]oxy} quinoxaline; 6-Chloro-3-(methyloxy)-5-quinoxalinol. (for a synthesis see WO2006021448 Example 93(f)) ( 0.45 g, 2.0 mmol ) was dissolved in dry DMF (10 ml), treated with sodium hydride ( 60 % dispersion in oil ) ( 80 mg, 2.0 mmol ) and left stirring at room temperature for 30 min. R-( - )-Glycidyl nosylate ( 0.62 g, 2.4 mmol) was added and <n="74"/>the reaction mixture left stirring under argon atmosphere at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer extracted with ethyl acetate ( 50 ml x 4 ), organics combined, dried ( MgSO4), filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient 0 - 40 % ethyl acetate in hexane. to give the titled compound as an off-white solid ( 0.45 g, 85 % ). MS (ES+), m/z 267 (MH+, 100%).

Reference： [1]Patent: WO2008/128953,2008,A1 .Location in patent: Page/Page column 72-73

70
[ 400613-89-0 ]
[ 115314-14-2 ]
(R)-2-[(cyclopropyl)(2-methoxyphenyl)methoxymethyl]oxirane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(Cyclopropyl)(2-methoxyphenyl)methanol (3.57 g) obtained in Step 1 was dissolved in N,N-dimethylformamide (50 ml), sodium hydride (960 mg, 60% oil) was added and the mixture was stirred for 3 min. To the resulting mixture was added (R)-glycidyl 3-nitrobenzenesulfonate (6.22 g) and the mixture was stirred at room temperature for 12 hr. The reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=88:12) to give the title compound (1.10 g).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3809 - 3813
[2]Patent: US2004/6130,2004,A1 .Location in patent: Page 20

71
[ 1083099-56-2 ]
[ 115314-14-2 ]
[ 1083099-50-6 ]

Yield	Reaction Conditions	Operation in experiment
98.09%	With potassium hydroxide; In N,N-dimethyl acetamide; at 19 - 20℃; for 2.5h;Product distribution / selectivity;	Example 25 Synthesis of (R) -1- (4-oxiranylmethoxy)phenyl-4- (4- trifluoromethoxybenzyloxy)piperidine31.26 kg of 1- (4-hydroxyphenyl) -4- (4- trifluoromethoxybenzyloxy)piperidine 4- methylbenzenesulfonic acid, 125 L of N, N- dimethylacetamide and 8.03 kg of potassium hydroxide were mixed, and stirred at room temperature. The mixture was mixed with 15.77 kg of (R) -oxiranylmethyl 3-nitrobenzenesulfonate, stirred at 19 to 20C for 2.5 hours, and cooled to 10C or less. The mixture was mixed with 0.904 kg of sodium dihydrogenphosphate dihydrate and 313 L of water, stirred at 50 to 60C for 0.5 hour; then, the crystal was filtered, washed with 156 L of water, and dried at 60C for 16 hours to obtain 24.06 kg of an ivory crystal target substance. Yield: 98.09%HPLC purity: 94.7% Optical purity: 99.5%ee (R-isomer) 1H-NMR (300MHz,CDCl3)=1.70-1.90(m,2H) , 1.98-2.12 (m, 2H) , <n="65"/>2.70-2.77 (m, IH) , 2.80-2.95 (m, 3H) , 3.28-3.35 (m, IH) , 3.35-3.50(111,2H)7 3.50-3.65 (m, IH) , 3.88-3.94 (m, IH) , 4.12-4.18 (m, IH) , 4.5S(S, 2H), 6.80-6.95 (m, 4H) , 7.19(d,2H,8.7Hz) , 7.38 (d, 2H, 8.8Hz)

Reference： [1]Patent: WO2008/140090,2008,A1 .Location in patent: Page/Page column 63-64

72
[ 1108184-03-7 ]
[ 115314-14-2 ]
[ 1108184-14-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With caesium carbonate; In dimethyl sulfoxide; at 20℃;	A mixture of 1-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (750 mg, 2.11 mmol), (R)-(-)-glycidyl nosylate (657 mg, 2.53 mmol) and cesium carbonate (1.03 g, 3.17 mmol) in methyl sulfoxide (6 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification by column chromatography (silica gel, ethyl acetate) gave the title compound (480 mg, 55%) as a yellow solid: 1H NMR (300 MHz, CDCl3) delta 8.09 (d, J=0.9 Hz, 1H), 7.76-7.72 (m, 5H), 7.65 (d, J=9.0 Hz, 1H), 7.52 (d, J=7.2 Hz, 1H), 7.47 (dd, J=9.0, 2.1 Hz, 1H), 6.92 (d, J=1.8 Hz, 1H), 6.53 (dd, J=6.9, 1.8 Hz, 1H), 4.79 (dd, J=15, 3.0 Hz, 1H), 4.48 (dd, J=15.3, 5.7 hz, 1H), 3.41-3.37 (m, 1H), 2.88 (app t, J=4.5 Hz, 1H), 2.60 (dd, J=4.5, 2.4 Hz, 1H).

Reference： [1]Patent: US2009/82359,2009,A1 .Location in patent: Page/Page column 55

73
[ 100-02-7 ]
[ 115314-14-2 ]
[ 125279-81-4 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5506 - 5521
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 5506 - 5521

74
[ 115314-14-2 ]
[ 50461-52-4 ]
[ 1170733-32-0 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of Compound 4; Compound 1 (220 mg, 1.0 mmol) was dissolved in anhydrous THF (10 mL). The solution was cooled to 0 C. and NaH (40 mg, 1.0 mmol, 60% in mineral oil) was added in one portion. The gray suspension was stirred at the same temperature for about 30 min until H2 ceased bubbling. To the above suspension at 0 C. was added dropwise a solution of compound 3 (280 mg, 1.1 mmol) in anhydrous THF (6 mL). The mixture was allowed to warm to rt and stirred overnight. The next morning, crushed ice (1-2 g) was added to quench the reaction, and the mixture was extracted with ethyl acetate (20 mL×3). The organic layers were combined and washed successively with saturated aqueous NH4Cl (20 mL×3), brine (20 mL×3) and dried over Na2SO4. After filtration and concentration under reduced pressure, the crude syrup was purified by flash column chromatography to give compound 4 (170 mg, 63%) as a brown solid.1H NMR (300 MHz, CDCl3) delta 7.74 (d, J=8.0 Hz, 1H), 7.64 (d, J=6.5 Hz, 1H), 7.28 (dd, J=6.5 Hz, J2=4.0 Hz, 2H), 7.14 (s, 1H), 6.21 (s, 1H), 3.41 (dd, J1=9.4 Hz, J2=6.2 Hz, 2H), 3.16-3.18 (m, 1H), 2.88 (dd, J1=8.3 Hz, J2=5.4 Hz, 2H), 2.80 (td, J=5.4 Hz, J2=4.4 Hz, 2H), 2.66-2.68 (m, 2H), 2.53 (t, J=2.4 Hz, 2H);13C NMR (75 MHz, CDCl3) delta 147.76, 144.21, 137.27, 131.08, 124.77, 124.20, 123.93, 123.26, 121.06, 119.67, 47.47, 46.45, 44.58, 42.65, 36.10, 27.34.

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 656 - 661
[2]Patent: US2009/182011,2009,A1 .Location in patent: Page/Page column 13

75
[ 6921-66-0 ]
[ 115314-14-2 ]
[ 1189360-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 20h;Inert atmosphere;	EXAMPLE 7 (R)-1-(4-Chloro-2-oxiranylmethoxy-phenyl)-ethanone In a 22 L, four-necked flask (equipped with a mechanical stirrer, thermocouple, Teflon stopper, and a argon inlet) was charged 4-chloro-2-hydroxy-acetophenone (13, 687.2 g, 4.03 mol) and N,N-dimethylformamide (14.0 L). To this solution was added potassium carbonate (613 g, 4.43 mol) and (R)-glycidyl m-nitrophenylsulfonate (1.045 kg, 4.03 mol). The reaction mixture was heated to 40 C. for 20 h (overnight) then cooled to room temperature and split into two portions. Each portion was poured into water (9 L) and extracted with methyl tert-butyl ether (32 L) and ethyl ether (2 L). The two organic phases were each washed with brine (24 L), dried (MgSO4), and concentrated in vacuo to yield crude product, which was used in subsequent steps without further purification. 1H NMR (CDCl3) delta ppm: 7.71 (d, J=8.5 Hz, 1H), 7.02 (dd, J=8.8, 1.7 Hz, 1H), 6.95 (d, J=1.8 Hz, 1H), 4.39 (dd, J=11.0, 2.8 Hz, 1H), 3.98 (dd, J=10.8, 6.1 Hz, 1H), 3.41 (m, 1H), 2.96 (t, J=4.4 Hz, 1H), 2.78 (dd, J=5.1, 2.7 Hz, 1H), 2.64 (s, 3H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 20h;	In a 22 L, four-necked flask (equipped with a mechanical stirrer, thermocouple, Teflon stopper, and a argon inlet) was charged 4-chloro-2- hydroxy-acetophenone (13, 687.2 g, 4.03 mol) and lambda/,lambda/-dimethylformamide (14.0 L). To this solution was added potassium carbonate (613 g, 4.43 mol) and (R)-glycidyl m-nitrophenylsulfonate (1 .045 kg, 4.03 mol). The reaction mixture was heated to 400C for 20 h (overnight) then cooled to room temperature and split into two portions. Each portion was poured into water (9 L) and extracted with methyl terf-butyl ether (3 x 2 L) and ethyl ether (2L). The two organic phases were each washed with brine (2 x 4 L), dried (MgSO4), and concentrated in vacuo to yield crude product, which was used in subsequent steps without further purification.1H NMR (CDCI3) delta ppm: 7.71 (d, J = 8.5 Hz, 1 H), 7.02 (dd, J = 8.8, 1.7 Hz, 1 H), 6.95 (d, J = 1.8 Hz, 1 H), 4.39 (dd, J = 1 1 .0, 2.8 Hz, 1 H), 3.98 (dd, J = 10.8, 6.1 Hz, 1 H), 3.41 (m, 1 H), 2.96 (t, J = 4.4 Hz, 1 H), 2.78 (dd, J = 5.1 , 2.7 Hz, 1 H), 2.64 (s, 3H). A small portion of the product prepared as described above was chromatographed (Isco silica - 40 g) to yield a white powder: MP: 79-800C.Optical Rotation: [alpha]D = -19.4 (c 2.02, MeOH, 23C). High-Resolution MS: (as CnH12O3CI, M+H) : Calculated: 227.48; Measured: 227.05

Reference： [1]Patent: US2009/247618,2009,A1 .Location in patent: Page/Page column 23-24
[2]Patent: WO2009/120192,2009,A2 .Location in patent: Page/Page column 54

76
[ 1189360-82-4 ]
[ 115314-14-2 ]
[ 1189360-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 40℃; for 12h;Inert atmosphere;	EXAMPLE 4 (R)-2-(2-Benzyloxy-5-chloro-phenoxymethyl)-oxirane In a 500 mL, three-necked flask (equipped with a magnetic stir bar, thermocouple, and a nitrogen inlet) was charged 2-benzyloxy-5-chloro-phenol (10, 11.3 g, 48.2 mmol), (R)-glycidyl m-nitrophenylsulfonate (11.3 g, 43.8 mmol), and N,N-dimethylformamide (200 mL). The reaction mixture was heated to 40 C. for 12 hrs, then cooled to room temperature and poured into water (300 mL). The aqueous phase was extracted with ethyl ether (3200 mL). The combined organic phases were washed with 1M sodium hydroxide (aq), brine (3100 mL), dried (MgSO4), and concentrated in vacuo to yield crude product as an oil. The oil was dissolved in 1:1 heptane-dichloromethane and loaded onto an Isco cartridge (120 g silica gel) and eluted to yield the title compound as an oil. 1H NMR (CDCl3) delta ppm: 7.38 (m, 5H), 6.94 (d, J=2.5 Hz, 1H), 6.85 (m, 2H), 5.11 (s, 2H), 4.28 (dd, J=11.4, 3.3 Hz, 1H), 4.01 (dd, J=11.3, 5.5 Hz, 1H), 3.38 (m, 1H), 2.89 (dd, J=5.1, 4.9 Hz, 1H), 2.77 (dd, J=5.0, 2.6 Hz, 1H).
	In N,N-dimethyl-formamide; at 40℃; for 12h;	In a 500 ml_, three-necked flask (equipped with a magnetic stir bar, thermocouple, and a nitrogen inlet) was charged 2-benzyloxy-5-chloro-phenol (10, 1 1 .3 g, 48.2 mmol), (R)-glycidyl m-nitrophenylsulfonate (1 1.3 g, 43.8 mmol), and lambda/,lambda/-dimethylformamide (200 ml_). The reaction mixture was heated to 400C for 12hrs, then cooled to room temperature and poured into water (300 ml_). The aqueous phase was extracted with ethyl ether (3 x 200 ml_). The combined organic phases were washed with 1 M sodium hydroxide (aq), brine (3 x 100 ml_), dried (MgSO4), and concentrated in vacuo to yield crude product as an oil. The oil was dissolved in 1 :1 heptane-dichloromethane and loaded onto an lsco cartridge (120 g silica gel) and eluted to yield the title compound as an oil.1H NMR (CDCI3) delta ppm: 7.38 (m, 5H), 6.94 (d, J = 2.5Hz, 1 H), 6.85 (m, 2H), 5.1 1 (s, 2H), 4.28 (dd, J = 1 1.4, 3.3 Hz, 1 H), 4.01 (dd, J = 1 1.3, 5.5 Hz, 1 H), 3.38 (m, 1 H), 2.89 (dd, J = 5.1 , 4.9 Hz, 1 H), 2.77 (dd, J = 5.0, 2.6 Hz, 1 H).

Reference： [1]Patent: US2009/247618,2009,A1 .Location in patent: Page/Page column 23
[2]Patent: WO2009/120192,2009,A2 .Location in patent: Page/Page column 52

77
[ 576-24-9 ]
[ 115314-14-2 ]
[ 198226-59-4 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3982 - 3993

78
[ 2373-31-1 ]
[ 115314-14-2 ]
(2R)-glycidyl-6-(4-methylcoumarinyl)ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		1.56 g (8.9 mmol) 6-hydroxy-4-methylcoumarin and 1.6 g potassium carbonate were combined in a solvent mixture composed of 30 mL dry dimethyl-formamide and 30 mL acetone. The resulting solution was heated to reflux, after which 2.5 g (9.6 mmol) <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> was added to the solution. The reaction mixture was heated at 50-60 C. for 3 hr with stirring. To the solution was added 30 mL ethyl acetate and 30 mL water, resulting in precipitate formation. The solid was filtered, and the organic phase was saved. The aqueous phase was extracted with 4×25 mL ethyl acetate. The combined organic phase was dried over sodium sulfate. After filtration, solvent evaporation yielded crude product as a solid. This material was recrystallized from ethyl acetate:ethanol:acetone (30:5:5) to yield 0.76 g (37% yield) product. Additional product was obtained from the mother liquor.

Reference： [1]Patent: US6800768,2004,B1 .Location in patent: Page column 26

79
[ 787585-39-1 ]
[ 115314-14-2 ]
[ 787585-40-4 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl 4-[2-((1R)-hydroxyethyl)phenoxy]benzoate (3.62 g) obtained in Step 2 was dissolved in tetrahydrofuran (15 ml). The mixture was ice-cooled and sodium hydride (471 mg, 60% in oil) was added. The mixture was stirred for 3 min. Then, (R)-glycidyl 3-nitrobenzenesulfonate (3.62 g) and dimethyl sulfoxide (3 ml) were added and the mixture was stirred overnight at room temperature. 10% Aqueous citric acid solution (80 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (150 ml). The organic layer was washed successively with water (50 ml) and saturated brine (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-3:1) to give the title compound (315 mg). 1H-NMR (300 MHz, deltappm, CDCl3) 7.99(2H, d, J=6.6 Hz) , 7.57(1H, m) 7.31-7.23(2H, m), 6.96-6.90(3H, m), 4.80(1H, d, J=6.6 Hz), 3.89(3H, s), 3.55(1H, m), 3.26(1H, m), 3.25(1H, m), 2.74(1H, m), 2.51(1H, m), 1.41(3H, d, J=6.6 Hz).

Reference： [1]Patent: US2005/32796,2005,A1 .Location in patent: Page/Page column 71

80
[ 115314-14-2 ]
5-bromo-2,3-difluoro-phenol [ No CAS ]
[ 702687-42-1 ]

Yield	Reaction Conditions	Operation in experiment
97%		Example 2a F F F I OH 0, acaione Fl OH F 0 1 /o,, o/ Br' Br onc Br i Br o o (R)-2- (5-BROMO-2, 3-DIFLUORO-PHENOXYMETHYL)-OXIRANE; To an acetone solution (0.1 M, 240 mL) of commercially available 5-bromo-2,3- difluorophenol (5.0 g, 23.93 mmol) was added K2CO3 (9.92 g, 71.77 mmol), and the mixture was heated to reflux for 30 min. After cooling this mixture to RT, (2R)- (-)-GLYCIDYL 3- nitrobenzenesulfonate (6.20 g, 23.93 mmol) was added, and the resulting mixture was heated to reflux overnight. After cooling to RT, the solids were removed by filtration and washed well with ethyl acetate. The filtrate was concentrated and partitioned between ethyl acetate and IN HC1. The organic portion was washed successively with 5% NAHCO3 AND brine, dried (MGSO4), filtered and concentrated to a solid. Purification by FCC (15% ethyl acetate/hexanes) gave the product as a white solid in 97% yield (6.19 g).
97%		General procedure: (a) (R)-2-(5-Bromo-2,3-difluoro-phenoxymethyl)-oxirane To an acetone solution (0.1 M, 240 mL) of commercially available 5-bromo-2,3-difluorophenol (5.0 g, 23.93 mmol) was added K2CO3 (9.92 g, 71.77 mmol), and the mixture was heated to reflux for 30 min. After cooling this mixture to RT, <strong>[115314-14-2](2R)-(-)-glycidyl 3-nitrobenzenesulfonate</strong> (6.20 g, 23.93 mmol) was added, and the resulting mixture was heated to reflux overnight. After cooling to RT, the solids were removed by filtration and washed well with ethyl acetate. The filtrate was concentrated and partitioned between ethyl acetate and 1N HCl. The organic portion was washed successively with 5% NaHCO3 and brine, dried (MgSO4), filtered and concentrated to a solid. Purification by FCC (15% ethyl acetate/hexanes) gave the product as a white solid in 97% yield (6.19 g).

Reference： [1]Patent: WO2005/30749,2005,A1 .Location in patent: Page/Page column 14-15
[2]Patent: US9227914,2016,B2 .Location in patent: Page/Page column 9

81
[ 7471-03-6 ]
[ 71916-97-7 ]
[ 115314-14-2 ]
(2S)-1-[(2-amino-1,3-benzothiazol-4-yl)oxy]-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step II : (2S)-1-[(2-Amino-1, 3-benzothiazol-4-yl) oxy]-3-(5-chloro-1'H, 3H-spiro [1-benzofuran- 2, 4'-piperidin]-1'-yl) propan-2-ol A mixture of 2-amino-1, 3-benzothiazol-4-ol (100 mg, 0.6 mmol), (2S)-oxiran-2-ylmethyl- 3-nitrobenzenesulfonate (156 mg, 0.6 mmol) and Cs2CO3 (195 mg, 0.6 mmol) in DMF (3 mL) was stirred at room temperature over night. The mixture was partitioned between ethyl acetate and H20. The organic layer was dried over Na2S04, and filtered. 5-Chloro- 3H-spiro[1-benzofuran-2, 4'-piperidine] (134 mg, 0.6 mmol) was added to the filtrate, and the solution was concentrated in vacuo. The residue was taken into ethanol (3 mL) and stirred at 75 °C for 3 h. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (0-2 percent methanol in CH2C12 containing 0.2percent ammonia) to give title compound (60 mg). 'H-NMR (400 MHz, DMSO-d6) : 5 7.41 (s, 2H); 7.24 (m, 2H); 7.09 (dd, J= 2.3, 8.5 Hz, 1H) ; 6.94 (t, J= 7.9 Hz, 1H) ; 6.84 (d, J= 8.1 Hz, 1H) ; 6.74 (d, J= 8.5 Hz, 1H) ; 4.82 (s, 1H) ; 4. 08 (m, 1H) ; 3.98 (m, 2H) ; 3.00 (s, 2H); 2.68-2. 38 (m, 6H); 1.80 (m, 4H). APCI-MS: m/z 446 [MH'].

Reference： [1]Patent: WO2005/54249,2005,A1 .Location in patent: Page/Page column 31

82
[ 98192-14-4 ]
[ 115314-14-2 ]
[ 1198606-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3.16667h;	(Step B) Synthesis of (S)-2-bromo-N-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide 2-Bromo-N-methylbenzenesulfonamide (10 g) obtained from above Example 1-1 Step A was dissolved in dimethylformamide (100 mL), and (R)-glycidyl 3-nitrobenzenesulfonate (WAKO, 11.4 g), and potassium carbonate (KANTO, 11.05 g) were added thereto, followed by stirring at 80 C. for 3 hours and 10 minutes. After cooling to room temperature, water was added to the reaction solution and extraction was carried out with ether. The organic layer was washed with water and brine in order, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain the target compound (8.63 g).

Reference： [1]Patent: US2010/22601,2010,A1 .Location in patent: Page/Page column 22

83
[ 115314-14-2 ]
[ 220509-74-0 ]
[ 1160524-47-9 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3484 - 3495

84
[ 121-51-7 ]
[ 57044-25-4 ]
[ 115314-14-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In toluene; at -10℃; for 2h;	Reaction 5.; C6H4ClNO2S R-glycidolC9H9NO6S 221.62 259.24Procedure: As in IN-SPL-C-11To R-glycidol, toluene and Et3N were added. Then Nitrosulfonyl chloride was added in lots at -100C and stirred for 2 hours. Following EtO Ac/water work up, the residue was purified by column chromatography.10Theoretical Yield: 17.54 g Yield Obtained: 15.5 g % Yield: 88 % 1H NMR: verified

Reference： [1]Patent: WO2010/14263,2010,A1 .Location in patent: Page/Page column 54

85
[ 100200-99-5 ]
[ 115314-14-2 ]
[ 394248-96-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With cesium fluoride; In N,N-dimethyl-formamide; for 48h;	Example 6OA. (i?)-2-((2-Methoxy-4-nitrophenoxy)methyl)oxirane[00249] To a solution of potassium 2-methoxy-4-nitrophenolate (6.0 g, 29.0 mmol) in DMF (30 mL) was added cesium fluoride (13.19 g, 87 mmol). After stirring Ih, (i?)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (8.26 g, 31.8 mmol) was added and the mixture was stirred for 2 days. The mixture was partially concentrated under reduced pressure, diluted with water and extracted with EtOAc. The combined organic extracts were washed with water, brine, dried (MgSO4), and concentrated. The residue was purified by chromatography (SiO2 solvent gradient 33-60%EtOAc/Hexanes) to give the Example 6OA (6.4 Ig, 98 % yield) as a white solid. LC- MS, [M+H]+ = 226. 1H NMR (CDCl3, 400 MHz) delta 7.89 (dd, J = 8.8 and 2.6 Hz, IH), 7.76 (d, J = 2.6 Hz, IH), 6.98 (d, J = 8.8 Hz, IH), 4.43 (dd, J = 11.4 and 2.6 Hz, IH), 4.08 (dd, J = 11.4 and 6.2 Hz, IH), 3.96 (s, 3H), 3.43 (m, IH), 2.95 (m, IH), 2.81 (m, IH).

Reference： [1]Patent: WO2010/42682,2010,A1 .Location in patent: Page/Page column 117

86
[ 20988-55-0 ]
[ 115314-14-2 ]
[ 1236375-64-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3809 - 3813

87
(cyclopropyl)(2-methylphenyl)methanol [ No CAS ]
[ 115314-14-2 ]
(R)-2-[(cyclopropyl)(2-methylpheny)methoxymethyl]oxirane [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3809 - 3813

88
[ 7471-03-6 ]
[ 115314-14-2 ]
[ 1528746-89-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 108 - 112

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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 115314-14-2 ] {[proInfo.proName]}

Quality Control of [ 115314-14-2 ]

Related Doc. of [ 115314-14-2 ]

Product Details of [ 115314-14-2 ]

Calculated chemistry of [ 115314-14-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 115314-14-2 ]

Application In Synthesis of [ 115314-14-2 ]

[ 115314-14-2 ] Synthesis Path-Upstream 1~4

[ 115314-14-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 115314-14-2 ]

Aryls

Sulfonates

Nitroes

Related Parent Nucleus of [ 115314-14-2 ]

Epoxides

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

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Inquiry

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[ 115314-14-2 ]

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[ 115314-14-2 ]