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Chemical Structure| 1700-31-8 Chemical Structure| 1700-31-8

Structure of 1700-31-8

Chemical Structure| 1700-31-8

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Product Details of [ 1700-31-8 ]

CAS No. :1700-31-8
Formula : C14H13BrO
M.W : 277.16
SMILES Code : C(C1=CC=CC=C1)OC2=CC(=CC=C2)CBr
MDL No. :MFCD01318307
InChI Key :ITJWNXBZSFIJTP-UHFFFAOYSA-N
Pubchem ID :1502047

Safety of [ 1700-31-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 1700-31-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 12
Fraction Csp3 0.14
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 70.26
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

9.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

3.03
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.35
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.86
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.99
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

4.42
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.93

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.59
Solubility 0.00713 mg/ml ; 0.0000257 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.26
Solubility 0.0153 mg/ml ; 0.0000551 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.31
Solubility 0.000135 mg/ml ; 0.000000485 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.9 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.02

Application In Synthesis of [ 1700-31-8 ]

* 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.

  • Downstream synthetic route of [ 1700-31-8 ]

[ 1700-31-8 ] Synthesis Path-Downstream   1~35

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  • [ 69944-62-3 ]
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  • [ 122488-53-3 ]
  • [ 122488-18-0 ]
  • 3
  • [ 1700-31-8 ]
  • [ 86653-16-9 ]
  • [ 140161-09-7 ]
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  • [ 1700-30-7 ]
  • [ 1700-31-8 ]
YieldReaction ConditionsOperation in experiment
97% With phosphorus tribromide; In diethyl ether; Synthesis of Compound 172 Preparation of (3-benzyloxy)benzyl bromide: To a solution of (3-benzyloxy)benzyl alcohol (3.0 g, 14.0 mmol) in anhydrous diethyl ether (50 mL) was added PBr3 (0.66 mL, 7.0 mmol) in one portion, and the resulting mixture was stirred at room temperature for 3 hours. The mixture was diluted with diethyl ether (60 mL) and washed with H2O (2*40 mL), saturated NaHCO3 (2*40 mL), and brine (2*40 mL). The ether layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford (3-benzyloxy)benzyl bromide (3.76 g, 97percent) as a pale yellow solid.
97% With phosphorus tribromide; In diethyl ether; Synthesis of Compound 172 Preparation of (3-benzyloxy)benzyl bromide: To a solution of (3-benzyloxy)benzyl alcohol (3.0 g, 14.0 mmol) in anhydrous diethyl ether (50 mL) was added PBr3 (0.66 mL, 7.0 mmol) in one portion, and the resulting mixture was stirred at room temperature for 3 hours. The mixture was diluted with diethyl ether (60 mL) and washed with H2O (2*40 mL), saturated NaHCO3 (2*40 mL), and brine (2*40 mL). The ether layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford (3-benzyloxy)benzyl bromide (3.76 g, 97percent) as a pale yellow solid.
89% With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 3h; Using the procedure reported by K. Thakkar et al., J. Med. Chem., 1993, 36 (20), 2950. [0500] Phosphorus tribromide (1.96 mL, 20.6 mmol) was added to a solution of 3-benzyloxybenzyl alcohol (4.29 g, 20 mmol) in anhydrous dichloromethane (90 mL) at 0° C. The mixture was stirred at 0° C. for 2 h and then at room temperature for 1 h. The reaction was poured onto ice/water (400 mL) and allowed to warm to room temperature. The aqueous solution was extracted with Et2O (5.x.100 mL) and the combined ethereal solution dried (MgSO4). Concentration in vacuo gave a light yellow oil which crystallised on standing to give OBS01018 as colourless needles (4.93 g, 89percent). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.9; m.p. 55-56° C. [Lit. (Petroleum ether): 55° C.]; 1H-NMR (400 MHz, CDCl3) 4.44 (2H, s), 5.05 (2H, s); 6.78 (1H, d, J=2), 6.93 (1H, m), 7.22 (1H, t, J=8), 7.40 (5H, m).
64% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 2h; 3-Hydroxybenzaldehyde (5.00 g, 0.041 mol) was dissolved in anhydrous acetonitrile (130 mL) under argon atmosphere. Cesium carbonate (20.01 g, 0.061 mol) was added and the suspension stirred for 5 min. Benzyl bromide (11.69 mL, 0.102 mol) was then added and the solution heated at reflux for 16 h. The solution was concentrated on rotary evaporator, water was added and the mixture was extracted with EtOAc. The organic phase was washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. Water was added and the mixture was extracted with CH2Cl2. The crude product was purified by flash chromatography on silica gel with hexanes/EtOAc (80/20) to yield 3a as a white solid (8.59 g). 1H NMR delta (CDCl3) 5.13 (s, 2H, PhCH2O), 5.33 (s, 2H, COOCH2Ph), 7.35-7.50 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O), 10.00 (s, 1H, PhCHO). The aldehyde 3a was dissolved in anhydrous THF (200 mL) under argon and cooled to 0 °C. Lithium aluminum hydride (1.55 g, 0.041 mol) was added in small portions and the solution stirred at room temperature for 2 h. The reaction was then quenched using water (0.8 mL), a 10percent wt aqueous NaOH solution (1.15 mL) and water again (1.9 mL) and left to settle. The suspension was then filtered and concentrated. Water was added and the mixture extracted with EtOAc, the organic phase dried over MgSO4, filtered and concentrated to yield 7.07 g crude alcohol 3b. 1H NMR delta (CDCl3) 4.68 (s, 2H, PhCH2OH), 5.08 (s, 2H, PhCH2O), 6.90-7.46 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O). Crude alcohol 3b (7.06 g) was dissolved in anhydrous CH2Cl2 (330 mL) and the solution cooled to 0 °C. Triphenylphosphine (17.28 g, 0.066 mol) and carbon tetrabromide (21.85 g, 0.066 mol) were then added and the solution stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phase was dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography on silica gel with hexanes/EtOAc (9/1) to yield 5.85 g (64percent) of bromide 3c. 1H NMR delta (CDCl3) 4.47 (s, 2H, PhCH2Br), 5.07 (s, 2H, PhCH2O), 6.90-7.46 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O); 13C NMR (75 MHz) delta (acetone-d6) 32.5, 69.4, 114.3, 114.8, 121.0, 127.0 (2.x.), 127.2, 127.8, 128.0, 129.3, 136.1, 138.6, 158.3.
56% With phosphorus tribromide; In diethyl ether; at 20℃; for 3h;Cooling with ice; In an ice cooled solution of 3-benzyloxy-phenylmethanol (2.14 g, 10 mmol) in Et2O (25 mL), PBr333 (1.41 mL, 15 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h and the reaction mixture was quenched by the addition of H2O (15 mL) in small portions at 0 °C. The aqueous phase was removed and the organic layer was washed with H2O, dried over Na2SO4 and evaporated in vacuo. The product was purified by column chromatography (silica gel) using petroleum ether (bp 40-60 °C)-EtOAc, 7:3 as eluent. Yield 1.5 g (56percent); yellow oil.1H NMR (CDCl3) delta: 7.42-6.82(m, 9H, Ph), 5.06(s, 2H, OCH2Ph), 4.46(s, 2H, BrCH2Ph).13C NMR delta: 159.0, 139.2, 136.7, 129.8, 128.6, 128.0, 127.5, 121.5, 115.4, 114.9 70.0(OCH2Ph), 33.4(BrCH2Ph).Anal. Calcd for C14H13BrO: C, 60.67; H, 4.73. Found: C, 60.46; H, 4.69.
In hexane; dichloromethane; Example 57 3-benzyloxybenzylbromide A solution of 3-benzyloxybenzyl alcohol (9.54 g) in methylene chloride (40 ml) with TMSBr (2.5 eq, 13 mL) was heated at reflux for 1 hr. After cooling, the reaction was concentrated and then reconcentrated 2 X with methylene chloride (40 ml). The residue was chromatographed on silica gel eluding first with hexane followed by 10percent methylene chloride in hexane to afford 3-benzyloxybenzyl bromide which solidifies on cooling. 5.75 g m.p. 38°-40°. 1H NMR 500 MHz (CDCl3) d 7.43-7.3 (m, 5H), 7.22 (t, J=8.1 Hz, 1H), 7.0-6.9 (m, 2H), 6.88 (ddd, J=8.1, 2.4, 0.6 Hz), 5.021 (s, 2H), 4.417 (s, 2H)
In hexane; dichloromethane; Example 57 3-benzyloxybenzylbromide A solution of 3-benzyloxybenzyl alcohol (2.04 g) in methylene chloride (20 mL) with TMS Bromide (2.5 eq. 3.14 mL) was heated at reflux for 6 hr. After cooling, the reaction was concentrated and then reconcentrated 2* from methylene chloride. The residue was chromatographed on silica gel with 5percent methylene chloride in hexane to afford 3-benzyloxybenzyl bromide (1.26 g) as an oil. 1 H NMR 500 MHz (CDCl3) d 7.43-7.3 (m, 5H), 7.22 (t, J=8.1 Hz, 1H), 7.0-6.9 (m, 2H), 6.88 (ddd, J=8.1, 2.4, 0.6 Hz, 1H), 5.021 (s, 2H), 4.417 (s, 2H)
In hexane; dichloromethane; Example 57 3-benzyloxybenzylbromide A solution of 3-benzyloxybenzyl alcohol (9.54 g) in methylene chloride (40 ml) with TMSBr (2.5 eq, 13 mL) was heated at reflux for 1 hr. After cooling, the reaction was concentrated and then reconcentrated 2 * with methylene chloride (40 ml). The residue was chromatographed on silica gel eluding first with hexane followed by 10percent methylene chloride in hexane to afford 3-benzyloxybenzyl bromide which solidifies on cooling. 5.75 g m.p. 38°-40°. 1 H NMR 500 MHz (CDCl3) d 7.43-7.3 (m, 5H), 7.22 (t, J=8.1Hz, 1H), 7.0-6.9 (m, 2H), 6.88 (ddd, J=8.1, 2.4, 0.6 Hz), 5.021 (s, 2H), 4.417 (s, 2H)
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 3h; Intermediate Ll. b.2 (Scheme 1.1) Step A: l-((3-(Bromomethyl)phenoxy)methyl)benzeneTo a solution of 3-benzyloxybenzyl alcohol (2 g, 9.3 mmol) and carbon tetrabromide (4 g, 12.1 mmol) in CH2Cl2 (70 mL), cooled to O°C, was added a solution of triphenylphosphine (2.9 g, 11.2 mmol) in CH2Cl2 (20 mL). The reaction was stirred at rt for 3 h and concentrated. Purification by flash chromatography (silica gel, 0-8percent EtOAc/hexanes) gave l-((3-(bromomethyl)phenoxy)methyl)benzene. 1H NMR (400 MHz, CDCl3) delta 7.39 (m, 5H), 7.25 (m, 1H), 7.00 (m, 2H), 6.92 (m, 1H), 5.06 (s, 2H), 4.46 (s, 2H).

  • 6
  • [ 1700-31-8 ]
  • [ 122-52-1 ]
  • [ 135203-60-0 ]
YieldReaction ConditionsOperation in experiment
at 150℃; for 3h; Example 17; Synthesis of 4-[3-(benzyloxy)benzylidene]-N-pyridin-3-ylpiperidine-1-carboxamide; Step 1; (3-Benzyloxy-benzyl)-phosphonic acid diethyl ester; 1-Benzyloxy-3-bromomethyl-benzene (4.95 g, 17.9 mmol) was treated with triethyl phosphite (3.2 mL, 18.7 mmol) and heated to 150° C. After 3 hours the reaction was cooled to room temperature and concentrated to give the title compound which was used without further purification (5.9 g).
  • 7
  • [ 1700-31-8 ]
  • [ 112968-75-9 ]
  • [ 96995-00-5 ]
  • [ 158665-01-1 ]
  • 8
  • [ 1700-31-8 ]
  • [ 57099-27-1 ]
  • 9
  • [ 1700-31-8 ]
  • [ 143-33-9 ]
  • [ 1860-58-8 ]
  • 10
  • [ 59311-29-4 ]
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  • (+/-)-2-<3'-(benzyloxy)benzyl>-3-<α,α-(1,3-dithiopropylene)-3'',4''-(methylenedioxy)benzyl>butyrolactone [ No CAS ]
  • 11
  • [ 1700-31-8 ]
  • [ 62096-77-9 ]
  • (3S,4S)-3-(3-Benzyloxy-benzyl)-4-[2-(3,4-dimethoxy-phenyl)-[1,3]dithian-2-yl]-dihydro-furan-2-one [ No CAS ]
  • 12
  • [ 1700-31-8 ]
  • [ 108102-77-8 ]
  • (3S,4R)-3-(3-Benzyloxy-benzyl)-4-(3,4-dimethoxy-benzyl)-dihydro-furan-2-one [ No CAS ]
  • 13
  • [ 1700-31-8 ]
  • [ 603-35-0 ]
  • 3-benzyloxybenzyltriphenylphosphonium bromide [ No CAS ]
  • 14
  • [ 1700-31-8 ]
  • [ 100516-54-9 ]
  • (3S,5S,6R)-3-(3-Benzyloxy-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester [ No CAS ]
  • 15
  • [ 1700-31-8 ]
  • [ 188978-55-4 ]
  • (4R,5R,6R)-6-Benzyl-5-hydroxy-1-(3-hydroxy-benzyl)-4-phenethyl-tetrahydro-pyrimidin-2-one [ No CAS ]
  • 16
  • [ 1700-31-8 ]
  • [ 188978-55-4 ]
  • (4R,5S,6R,7R)-4,7-Dibenzyl-3-(3-benzyloxy-benzyl)-5-hydroxy-1,3-diaza-bicyclo[4.1.0]heptan-2-one [ No CAS ]
  • Acetic acid (4R,5S,6R,7R)-4,7-dibenzyl-3-(3-benzyloxy-benzyl)-2-oxo-1,3-diaza-bicyclo[4.1.0]hept-5-yl ester [ No CAS ]
  • (4R,5S,6R,7R)-4,7-Dibenzyl-3-(3-benzyloxy-benzyl)-5-(3-benzyloxy-benzyloxy)-1,3-diaza-bicyclo[4.1.0]heptan-2-one [ No CAS ]
  • 17
  • [ 1700-31-8 ]
  • [ 113806-28-3 ]
  • [ 216491-37-1 ]
  • 18
  • [ 1700-31-8 ]
  • (3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-ylmethyl]-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]
  • (3aS,4R,8R,8aS)-4,8-Dibenzyl-5-(3-benzyloxy-benzyl)-2,2-dimethyl-7-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-ylmethyl]-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]
  • 19
  • [ 1700-31-8 ]
  • [ 497-23-4 ]
  • 1,2-Bis-benzyloxy-4-(bis-phenylsulfanyl-methyl)-benzene [ No CAS ]
  • (3S,4S)-3-(3-Benzyloxy-benzyl)-4-[(3,4-bis-benzyloxy-phenyl)-bis-phenylsulfanyl-methyl]-dihydro-furan-2-one [ No CAS ]
  • 20
  • [ 1700-31-8 ]
  • [ 497-23-4 ]
  • 1,2-Bis-benzyloxy-3-(bis-phenylsulfanyl-methyl)-benzene [ No CAS ]
  • (3S,4S)-3-(3-Benzyloxy-benzyl)-4-[(2,3-bis-benzyloxy-phenyl)-bis-phenylsulfanyl-methyl]-dihydro-furan-2-one [ No CAS ]
  • 21
  • [ 1700-31-8 ]
  • [ 497-23-4 ]
  • 1,4-Bis-benzyloxy-2-(bis-phenylsulfanyl-methyl)-benzene [ No CAS ]
  • (3S,4S)-3-(3-Benzyloxy-benzyl)-4-[(2,5-bis-benzyloxy-phenyl)-bis-phenylsulfanyl-methyl]-dihydro-furan-2-one [ No CAS ]
  • 23
  • [ 1700-31-8 ]
  • [ 110117-71-0 ]
  • (2R,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine [ No CAS ]
  • [ 247186-19-2 ]
  • 24
  • [ 1700-31-8 ]
  • 2-(3-benzyloxy-benzylamino)-6-<i>tert</i>-butoxycarbonylamino-hexanoic acid methyl ester [ No CAS ]
  • [ 247203-78-7 ]
  • 25
  • [ 1700-31-8 ]
  • [ 305647-02-3 ]
  • (S)-2-{(3-Benzyloxy-benzyl)-[(E)-3-(4-phenoxy-phenyl)-allyl]-amino}-6-tert-butoxycarbonylamino-hexanoic acid methyl ester [ No CAS ]
  • 26
  • [ 1700-31-8 ]
  • 6-<i>tert</i>-butoxycarbonylamino-2-{3-[3-(4-<i>tert</i>-butyl-phenoxy)-phenyl]-allylamino}-hexanoic acid methyl ester [ No CAS ]
  • 2-((3-benzyloxy-benzyl)-{3-[3-(4-<i>tert</i>-butyl-phenoxy)-phenyl]-allyl}-amino)-6-<i>tert</i>-butoxycarbonylamino-hexanoic acid methyl ester [ No CAS ]
  • 27
  • [ 1700-31-8 ]
  • [ 99-76-3 ]
  • [ 814920-59-7 ]
  • 28
  • [ 1700-31-8 ]
  • [ 96995-00-5 ]
  • 2-butenolide [ No CAS ]
  • [ 96995-01-6 ]
  • 29
  • [ 1700-31-8 ]
  • [ 116174-79-9 ]
  • [ 286459-64-1 ]
  • 30
  • [ 1700-31-8 ]
  • [ 148869-66-3 ]
  • [ 537674-63-8 ]
YieldReaction ConditionsOperation in experiment
28% With sodium hydride; In DMF (N,N-dimethyl-formamide); at 20℃; 4-[(3-Benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (OBS01019, STX675) To a suspension of NaH (60percent dispersion in oil, 0.22 g, 5.4 mmol) in anhydrous DMF (20 mL) at room temperature was added a solution of 4-[(4-cyanophenyl)amino]-4H-[1,2,4]triazole (see LWO02023) (1.0 g, 5.4 mmol) in anhydrous DMF (4 mL) and the mixture stirred under a positive flow of dry nitrogen for 1 h. The orange-yellow suspension was then treated with a solution of OBS01018 (1.57 g, 5.66 mmol) in anhydrous DMF (5 mL) and the mixture was stirred at room temperature overnight. The mixture was transferred to a separating funnel and diluted with EtOAc (100 mL). The organic layer was washed with water (4*100 mL), brine (100 mL), and dried (MgSO4). Concentration in vacuo gave a residue which was recystallised from i-PrOH to give OBS01019 as a white solid (0.58 g, 28percent). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.15 (blue fluorescence at 254 nm); 1H-NMR (400 MHz, CDCl3) 4.85 (2H, s), 5.03 (2H, s); 6.62 (2H, AA'BB'), 6.77 (1H, d, J=7.8), 6.79 (1H, d, J=2.4), 6.96 (1H, dd, J=7.8, 2.4), 7.26 (11H, t, J=7.8), 7.34-7.37 (5H, m), 7.57 (2H, AA'BB'), 8.04 (2H, s); LC-MS: tR=6.81 min, M+H=382 (Waters 2790 Alliance HPLC/ZQ MicroMass spectrometer with PDA detector using APCI, gradient elution: 5:95 MeCN/H2O-95:5 MeCN/H2O over 10 mins then 95:5 MeCN/H2O-5:95 MeCN/H2O using Waters "Symmetry" C18 (packing: 3.5 mum), 100 mm column); HPLC (Waters 717+Autosampler with PDA detector, using Waters "Symmetry" C18 (packing: 3.5 mum), 4.6*150 mm column, 90:10 MeOH/H2O) tR=2.27 min (98percent purity).
28% 4- [(3-Benzyloxybenzyl)(4-cyanoplzenyl)amino]-4H-[1,2,4]triazole;To a stirred suspension of NaH (60percent dispersion in oil, 0.22 g, 5.4 mmol) in anhydrous DMF (5 mL) was added a solution of 4-[(4-cyanophenyl)amino]-4H-[1,2,4]triazole (1.0 g, 5.68 mmol) in anhydrous DMF (3 mL) and the mixture stirred at r. t. for 0.5h. A solution of <strong>[1700-31-8]3-benzyloxybenzyl bromide</strong>[Thakkar, 1993] (1.57 g, 5.66 mmol) in anhydrous DMF (2 mL) was then added and the mixture heated at 80 - 90 °C overnight. The mixture was cooled, diluted with EtOAc (50 mL), washed with water (4 x 100 mL), brine (100 mL) and dried (Na2S04). Concentration in vacuo an orange residue which was purified by chromatography [Si02, EtOAc/n-hexane (1:1)] and to give 4-[(3- benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole as a colourless solid (0.58 g, 28percent) after crystallisation; No.H (400 MHz, CDCl3) 4.85 (s, 2H), 5.03 (s, 2H) ; 6.62 (AA'BB', 2H), 6.77 (d, J= 7.8,1H), 6.79 (d, J= 2.4,1H), 6.96 (dd, J= 7.8,2.4, 1H), 7.26 (t, J = 7.8, 1H), 7.34 - 7.37 (m, 5H), 7.57 (AA'BB', 2H), 8.04 (s, 2H) ; LC-MS (APCI+) tR = 6.81 min, m/z = 382 (M+H); HPLC tR = 2.27 min (98percent).
  • 31
  • [ 1700-31-8 ]
  • [ 107819-90-9 ]
  • [ 641611-53-2 ]
  • 32
  • phosphoric acid 3-benzyloxy-benzyl ester diethyl ester [ No CAS ]
  • [ 1700-31-8 ]
  • 33
  • [ 3770-50-1 ]
  • [ 1700-31-8 ]
  • [ 915700-93-5 ]
  • 34
  • [ 1700-31-8 ]
  • [ 537674-64-9 ]
  • 35
  • [ 1700-31-8 ]
  • sulfamic acid 3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-methyl}-phenyl ester [ No CAS ]
 

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