[ CAS No. 86123-95-7 ] {[proInfo.proName]}

Name: 86123-95-7|(R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid|97%
Brand: Ambeed
SKU: A122750
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Quality Control of [ 86123-95-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 86123-95-7 ]

CAS No. :	86123-95-7	MDL No. :	MFCD08063987
Formula :	C₉H₁₇NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RFGMSGRWQUMJIR-ZCFIWIBFSA-N
M.W :	219.24	Pubchem ID :	27281801
Synonyms :

Calculated chemistry of [ 86123-95-7 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.75
TPSA :	84.86 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) :	-7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	0.41
Log Po/w (WLOGP) :	0.61
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	-0.14
Consensus Log Po/w :	0.55

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.0
Solubility :	22.1 mg/ml ; 0.101 mol/l
Class :	Very soluble
Log S (Ali) :	-1.76
Solubility :	3.82 mg/ml ; 0.0174 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.79
Solubility :	35.2 mg/ml ; 0.161 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.97

Safety of [ 86123-95-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 86123-95-7 ]

* 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 [ 86123-95-7 ]
Downstream synthetic route of [ 86123-95-7 ]

[ 86123-95-7 ] Synthesis Path-Upstream 1~11

1
[ 3262-72-4 ]
[ 77-78-1 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -10 - 5℃; for 1 h; Stage #2: at 0 - 5℃; for 9 h;	A solution of N-Boc-D-serine (22g, 0.107 mol) in dry tetrahydrofuran (352ml) was cooled to <-10°C under a nitrogen atmosphere. To this was added via a dry addition funnel 15percent w/w n-butyllithium in hexanes (134ml, 0.216mol) keeping the temperature <10°C. The resultant slurry was aged for 1 hour at 0- 5°C. Dimethyl sulphate (12.1ml, 0.128mol) was added keeping the temperature at 0-5^°C and the reaction mixture aged at 0-5^°C for 9 hours. The reaction was quenched by the addition of water (110ml), basified to pH 10-13 with 30percent sodium hydroxide (3ml) and the tetrahydrofuran/hexane evaporated in vacuo. The residue was washed with toluene (44ml) and then acidified to a pH of <3.5 with 50percent citric acid. The acidified aqueous phase was extracted with methylene chloride (2x91 ml, 1x66ml) and the combined C936 extracts dried by azeotropic distillation. Yield on evaporation 23.7g, 100percent. HPLC purity 90.0percent, Chiral purity 100percent.
100%	Stage #1: With sodium hydroxide In water; toluene at 10℃; for 0.5 h; Stage #2: at 10℃; for 1 h;	A suspension of N-Boc-D-serine (22g, 0.107 mol) and tetrabutylammonium bromide (1.3g, 0.004mol) in toluene (110ml) was cooled to <10^°C. To this was added 20percent sodium hydroxide (17.6ml, 0.107mol) keeping the temperature <10°C and the resultant mixture was aged for 30 minutes at <10°C. Dimethyl sulphate (40.6ml, 0.429mol) and 50percent sodium hydroxide (25.4ml, 0.485mol) were added keeping the temperature <10^°C and the reaction mixture aged at 10°C for 1 hour. Water (66ml) was added to the mixture and the phases separated. The aqueous layer was acidified to a pH of <3.5 with 50percent citric acid, extracted with methylene chloride (2x91 ml, 1x66ml) and the combined C936 extracts dried by azeotropic distillation. (Yield on evaporation 27.5g, 100percent, HPLC purity 96.3percent, Chiral purity 98.1percent).
100%	With sodium hydroxide In water at 0 - 10℃; for 6 h;	The above prepared compound of formula I (20.5g, 0 . 100mol) cooling the aqueous solution to 0-10°C. Maintain 0-10°C, at the same time by adding drops of sulfuric acid dimethyl ester (50.5g, 0 . 400mol) and 50percent sodium hydroxide (36.0g, 0 . 450mol), reaction mixture in 0-10 °C reaction 6 hours. After the reaction, the reaction liquid maintain 0-10°C, with 50percent citric acid dyeworks to pH= 2-3, then with dichloromethane (1×123 ml, 2×82 ml) to extract and after drying with anhydrous sodium sulfate is distilled under reduced pressure to dry obtains the type compound II 21.9g (yield 100percent, HPLC purity 92.9percent, chiral purity 98.0percent).

83%	Stage #1: With tetrabutylammomium bromide; sodium hydroxide In toluene for 0.5 h; Cooling with ice Stage #2: With sodium hydroxide In toluene at 10℃; for 3 h; Stage #3: With citric acid In water	Synthesis of (R)-2-N-Boc-amino-3-methoxypropanoic acid[0155] A suspension of N-Boc-D-serine (17.6 g, 86 mmol) and tetrabutylammonium bromide (1.04 g, 3.23 mmol) in toluene (90 mL) was cooled with an ice-bath with stirring. To the reaction mixture was added 20percent sodium hydroxide (14 mL, 86 mmol) and the resulting mixture was stirred for thirty minutes. Dimethyl sulphate (43.3 g, 343 mmol) and 50percent sodium hydroxide (20.3 mL, 388 mmol) were added and the reaction mixture was stirred at < 10 °C for 3 hours. Water (60 ml) was then added to the mixture and the resulting two phases were separated. The aqueous phase was washed with dichloromethane (100 mL x 2). The aqueous phase was then acidified to a pH of <3.5 with 50percent citric acid and extracted with methylene chloride (100 mL ^χ 3). The organic phases were combined, dried over sodium sulfate, filtered, and solvent removed under reduced pressure to afford a colorless oil (15.6 g, yield: 83percent, purity >95percent). 1H NMR (500 MHz, CDC1₃) δ 1.45 (s, 9H), 3.37 (s, 3H), 3.62 (m, 1H), 3.85 (m, 1H), 4.43 (m, 1H), 5.42 (d, 1H). LC-MS (m/z) calculated 219.1 , found 242.0 [M + Naf.
87 g	With sodium hydroxide In water at 0 - 5℃;	Into a 2 L, four-necked RB flask was charged 90 ml of water and 40 g of sodium hydroxide. D-Serine is added to the solution at 20-25° C. Boc anhydride (150 g) is slowly added to the reaction mass keeping the temperature below 20° C. The reaction mass was allowed to reach 25-30° C. and maintained for 16 h. TLC of the reaction mass showed the presence of D-serine content at <1.0percent level. The reaction mass is cooled to 0-5° C. and started the simultaneous addition of aqueous sodium hydroxide (104 g of sodium hydroxide dissolved in 100 ml of water) and dimethyl sulphate (300 g) through addition funnels keeping the temperature below 5° C. The reaction mass was maintained at same temperature till the completion of reaction. The reaction mass is diluted with water and extracted the product into diisopropyl ether. Aqueous layer is neutralized with citric acid to get <3.5 pH. The reaction mass is extracted with diisopropyl ether and distilled of solvent to get 87 g of title compound as an oil.
34.5 g	With sodium hydroxide In water at 5 - 10℃; for 14 h;	To a stirred aqueous solution of sodium hydroxide (23.1 g of NaOH in 150 ml of water) was added D-serine (30 g) lot wise at 2G-25°C and BOC anhydride (74.7 g) at 10-15°C. The traction mixture was stirred at 20-25 ⁰C for 10 hours. Sodium hydroxide pellets (11.4g) was added to the reaction mixture at 5-10°C and stirred for another 30 mins. To the resulting reaction mixture was slowly added dimethylsulphate (340 ml) and aqueous solution of sodium hydroxide (91.0 g NaOH in 1 10 mL of water) at 5-10°C over 4 hours and then stirred for 10 hrs. The reaction mixture was acidified to pH -1 -2 with 2percent hydrochloric acid solution at 0-5°C and extracted with methylene chloride (300 ml). Separating organic layer, aqueous layer was extracted with methylene chloride (100 mL). The combined organic layer was concentrated under vacuum. The obtained residue was dissolved in methyl tert-butyl ether (83.25 mL) at 60-65°C. To the resulting solution was added H-hexane (466.2 mL) at 20-25°C and mixture was stirred for 10-12h. The solid was filtered and dried to provide the title compound as white solid. Weight: 34.5 g Yield: 55.29percent.

Reference： [1] Patent: WO2006/37574, 2006, A1, . Location in patent: Page/Page column 17
[2] Patent: WO2006/37574, 2006, A1, . Location in patent: Page/Page column 17-18
[3] Patent: CN104030943, 2016, B, . Location in patent: Paragraph 0103; 0104
[4] Patent: WO2012/51551, 2012, A1, . Location in patent: Page/Page column 36-37
[5] Tetrahedron, 2010, vol. 66, # 29, p. 5384 - 5395
[6] Patent: WO2011/95995, 2011, A1, . Location in patent: Page/Page column 10-11
[7] Patent: WO2011/99033, 2011, A1, . Location in patent: Page/Page column 42
[8] Patent: WO2012/46245, 2012, A1, . Location in patent: Page/Page column 7-8
[9] Patent: US2013/35508, 2013, A1, . Location in patent: Paragraph 0031
[10] Patent: WO2014/155264, 2014, A1, . Location in patent: Page/Page column 11-12

2
[ 862372-14-3 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With lithium hydroxide; water In tetrahydrofuran at 20℃; for 4 h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃;	Methyl N-(tert-butoxycarbonyl)-O-methyl-D-serinate (2.0 g, 85. 7 mmol) was dissolved in tetrahydrofuran (40 ml) and water (20 ml) and lithium hydroxide mono hydrate (1. 8 g, 42.9 mmol) added. The mixture was stirred for 4 hours at room temperature, concentrated under reduced pressure to remove most of the tetrahydrofuran and then acidified by the addition of concentrated hydrochloric acid. The solution was extracted with ethyl acetate (three times). The combined organics were dried (MgS04), filtered and evaporated under reduced pressure to give N-(tert-butoxycarbonyl)-O-methyl-D-serine (1.9 g, 100percent) as a colourless oil; IH NMR spectrum : (DMSO d6) 1.37 (s, 9H), 3.23 (s, 3H), 3.53 (m, 2H), 4. 18 (m, 1H), 6.87 (d, 1H), 12.60 (brs, 1H).

Reference： [1] Patent: WO2005/75439, 2005, A1, . Location in patent: Page/Page column 127

3
[ 3262-72-4 ]
[ 80-48-8 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With potassium hydroxide In toluene at 0 - 5℃; for 0.5 h; Stage #2: With tetrabutylammomium bromide In toluene at 0 - 5℃; for 8 h;	In a 1000 mL three-necked flask,400 mL of toluene and 40 g of N-tert-butoxycarbonyl-D-serine (Boc-D-serine)The stirring temperature was lowered to 0-5 ° C,36.5 g of 30percent potassium hydroxide solution was added dropwise.After stirring for 30 minutes,Then 72.65 g of methyl p-toluenesulfonate was added,Tetrabutylammonium bromide 4g,Then 43.68 g of 50percent potassium hydroxide solution was added dropwise.After reaction at 0-5 ° C for 8 hours,Add water 200mL and layered,The aqueous layer was washed with 100 mL of toluene,Discard the organic layer.The combined aqueous layers were then cooled to below 15 [deg.] C and acidified with 50percent phosphoric acid to pH = 2-3.5,Extraction with dichloromethane (200 mL * 3)The combined organic layers were added 30g of anhydrous sodium sulfate and stirred overnight.The next day filterThe filtrate was concentrated to dryness under reduced pressure,42.9 g of light yellow oil,Yield: 100percent, HPLC purity: 98.0percent, Chiral purity: 99.4percent.

Reference： [1] Patent: CN106699595, 2017, A, . Location in patent: Paragraph 0036; 0037

4
[ 3262-72-4 ]
[ 74-88-4 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide In water at 0 - 10℃; for 6 h;	The above prepared compound of formula I (20.5g, 0 . 100mol) cooling the aqueous solution to 0-10°C, maintain 0-10°C, drop at the same time add iodomethane (28.4g, 0 . 20mol) and 50percent sodium hydroxide (36.0g, 0 . 450mol), reaction mixture in 0-10 °C reaction 6 hours, after the reaction, the reaction liquid maintain 0-10°C, with 50percent citric acid dyeworks to pH= 2-3, then with dichloromethane (1×123 ml, 2×82 ml) extraction and drying with anhydrous sodium sulfate, then distilled under reduced pressure to dry obtains the type compound II 21.9g (yield 100percent, chiral purity 98.5percent).

Reference： [1] Patent: CN104030943, 2016, B, . Location in patent: Paragraph 0140; 0141
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 23, p. 5817 - 5822
[3] Patent: WO2012/46245, 2012, A1, . Location in patent: Page/Page column 8

5
[ 74-88-4 ]
[ 86123-95-7 ]

Reference： [1] Patent: WO2005/111029, 2005, A1, . Location in patent: Page/Page column 168-169

6
[ 67-56-1 ]
[ 3262-72-4 ]
[ 74-88-4 ]
[ 86123-95-7 ]

Reference： [1] Patent: WO2005/111014, 2005, A1, . Location in patent: Page/Page column 132-133

7
[ 24424-99-5 ]
[ 86123-95-7 ]

Reference： [1] Patent: WO2011/99033, 2011, A1,
[2] Patent: WO2012/46245, 2012, A1,
[3] Patent: WO2012/46245, 2012, A1,
[4] Patent: WO2014/155264, 2014, A1,
[5] Patent: CN104030943, 2016, B,
[6] Patent: CN104030943, 2016, B,

8
[ 721928-19-4 ]
[ 86123-95-7 ]

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5802 - 5803

9
[ 108149-63-9 ]
[ 86123-95-7 ]

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5802 - 5803

10
[ 100-46-9 ]
[ 86123-95-7 ]
[ 880468-89-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78℃; Inert atmosphere Stage #2: at -78 - 20℃; for 1 h;	To a solution of acid (R)-9 (0.7 g, 3.2 mmol) in dry THF was added N-methylmorpholine (0.43 mL, 3.8 mmol) at -78 °C under an argon atmosphere. After 5 min, isobutyl chloroformate (0.5 mL, 3.8 mmol) was added and stirred for another 5 min. To this reaction mixture benzylamine (0.4 mL, 3.8 mmol) was added at -78 °C after which the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was filtered, and washed with ethylacetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, petroleum ether/acetone, 85:15) to yield (R)-10 as a colorless solid (0.9 g, 90percent); mp 63-64 °C; (c 0.9, CHCl₃); IR (CHCl₃, cm^-1): ν_max 3683, 3431, 3020, 2931, 2401, 1714, 1523, 1496, 1368, 1165, 1119, 928, 758, 669; ¹H NMR (200 MHz, CDCl₃): δ_H 1.43 (s, 9H), 3.37 (s, 3H), 3.47-3.54 (dd, J = 9.2, 6.1 Hz, 1H), 3.82 (dd, J = 9.3, 3.7 Hz, 1H), 4.27 (m, 1H), 4.47 (d, J = 5.1 Hz, 1H), 5.41 (br s, 1H), 6.77 (m, 1H), 7.22-7.37 (m, 5H); ¹³C NMR (50 MHz, CDCl₃): δ_C 170.3 (CO), 155.5 (CO), 137.9 (C), 128.7 (CH, 2 carbons), 127.5 (CH, 3 carbons), 80.4 (C), 72.1 (CH₂), 59.1 (CH₃), 54.0 (CH), 43.5 (CH₂), 28.3 (CH₃, 3 carbons); MS: m/z 331 [M+Na]⁺.
90%	With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78 - 30℃; for 1 h; Inert atmosphere	Example-5 Synthesis of (R)-tert-butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate (R)-9 To a solution of acid (R)-8 (0.7 g, 3.2 mmol) in dry THF was added N-methylmorpholine (0.43 mL, 3.8 mmol) at -78° C. under argon atmosphere. After 5 min, isobutyl chloroformate (0.5 mL, 3.8 mmol) was added and stirred the content for another 5 min. To this reaction mixture benzylamine (0.4 mL, 3.8 mmol) was added at -78° C. and allowed the reaction mixture to stir at 30° C. for 1 h. After completion of the reaction, reaction mixture was filtered, washed with ethylacetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, petroleum ether/acetone, 85:15) to yield (R)-9 as colorless solid (0.9 g, 90percent). m.p 63-64° C.; [α]²⁵_D=-20.5 (c 0.9, CHCl₃); IR (CHCl₃, cm^-1): v_max 3683, 3431, 3020, 2931, 2401, 1714, 1523, 1496, 1368, 1165, 1119, 928, 758, 669; ¹H NMR (200 MHz, CDCl₃): δ_H 1.43 (s, 9H), 3.37 (s, 3H), 3.47-3.54 (dd, J=9.2, 6.1 Hz, 1H), 3.82 (dd, J=9.3, 3.7 Hz, 1H), 4.27 (m, 1H), 4.47 (d, J=5.1 Hz, 1H), 5.41 (bs, 1H), 6.77 (m, 1H), 7.22-7.37 (m, 5H); ¹³C NMR (50 MHz, CDCl₃): δ_C 170.3 (CO), 155.5 (CO), 137.9 (C), 128.7 (CH, 2 carbons), 127.5 (CH, 3 carbons), 80.4 (C), 72.1 (CH₂), 59.1 (CH₃), 54.0 (CH), 43.5 (CH₂), 28.3 (CH₃, 3 carbons); MS: m/z 331 [M+Na]⁺.
90%	Stage #1: With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 0.0833333 h; Inert atmosphere Stage #2: With isobutyl chloroformate In tetrahydrofuran at -78 - 20℃; for 1 h; Inert atmosphere	To a solution of acid 5 (0.985 g, 4.49 mmol) in dry THF (10ml) was added N-methylmorpholine (0.6 mL, 5.39 mmol) at -78 °C under an argon atmosphere.After 5 min, isobutyl chloroformate (0.7 mL, 5.39 mmol)was added and stirred for another 5 min. To this reaction mixture benzyl amine (0.6 mL, 5.39 mmol) was added at -78 °C andthe reaction mixture was allowed to come up to room temperature and stirred foranother 1 h. After completion of the reaction (TLC), the reaction mixture wasfiltered through a pad of celite, and washed with ethyl acetate (20 mL). Thesolvent was removed under reduced pressure and the crude reaction mixture wassubjected to flash chromatography (CombiFlash R_f200i, Teledyne Isco) using RediSep silica gel column (12 g) eluting with petroleum ether–EtOAc (3:2,isocratic) to yield 6as a white solid (1.24 g, 90percent); R_f0.35 (40percent EtOAc inpetroleum ether); mp 63-64 °C [Lit.63-64 °C³]; [α]_D²⁶ -24.3 (c 1.04, CHCl₃) [Lit. [α]_D²⁶-20.5 (c 0.9, CHCl₃)³]; IR (CHCl₃) u_max:3428, 3345, 3017, 2933, 2405, 1708, 1671, 1493, 1365, 1220, 1167, 1116, 1075,1025, 922, 860, 762, 668 cm^-1; ¹H NMR (200 MHz, CDCl₃) δ: 7.40-7.19 (m, 5H), 6.78 (brs, 1H),5.55-5.33 (m, 1H), 4.48 (d, J = 4.3 Hz, 2H), 4.27 (brs, 1H), 3.84 (dd, J= 3.9, 9.2 Hz, 1H), 3.50 (dd, J = 6.2, 9.1 Hz, 1H), 3.36 (s, 3H), 1.43(s, 9H); ¹³C NMR (50 MHz,CDCl₃) δ: 170.3,155.5, 138.0, 128.7, 127.5, 80.4, 72.1, 59.1, 43.5, 28.3; HRMS (ESI): m/z calcdfor C₁₆H₂₄N₂O₄Na [M + Na]⁺331.1628; found: 331.1612.

46.4%

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2 h; Cooling with ice

Synthesis of (R)-N-Benzyl-2-Boc-amino-3-methoxypropionamide[0157] (R)-2-N-Boc-amino-3-methoxypropanoic acid (15.0 g, 68.4 mmol), phenylmethanamine (7.33 g, 68.4 mmol), and DMAP (4.17 g, 34.2 mmol) were dissolved in DCM (150 mL). The solution was cooled in an ice-bath and EDC (21 .21 g, 137 mmol) was added dropwise to the solution. Once addition was complete, the reaction mixture stirred at warmed to room temperature and stirred for two hours. Then DCM (200 ml) was added to the mixture. The DCM organic phase was washed with H₂0 (200 mL x 1 ), 0.5 N HC1 (200 mL x 2), 5percent sodium bicarbonate (200 mL ^χ 2) and water (200 mL x 2). The organic phase was dried over sodium sulfate, filtered, and solvent removed under reduced pressure. The desired product was obtained as a colorless semi-solid with a purity >95percent (9.8 g, 46.4percent). NMR (500 MHz, CDC1₃) δ 1.46 (s, 9H), 3.38 (s, 3H), 3.51 (m, 1H), 3.86 (d, 1 H), 4.30 (br., 1H), 4.50 (s, 2H), 5.42 (br., 1H), 6.74 (br., 1H), 7.28 (m, 3H), 7.35 (m, 2H). LC-MS (m/z) , calculated. 308.2, found 309.1 [M + H]⁺, 331.1 [M + Naf.

Reference： [1] Tetrahedron Asymmetry, 2011, vol. 22, # 12, p. 1353 - 1357
[2] Patent: US2014/12044, 2014, A1, . Location in patent: Paragraph 0074; 0075
[3] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5802 - 5803
[4] Patent: WO2012/51551, 2012, A1, . Location in patent: Page/Page column 36-37
[5] Patent: WO2006/37574, 2006, A1, . Location in patent: Page/Page column 18
[6] Patent: WO2011/99033, 2011, A1, . Location in patent: Page/Page column 42
[7] Patent: WO2012/46245, 2012, A1, . Location in patent: Page/Page column 9

11
[ 86123-95-7 ]
[ 880468-89-3 ]

Reference： [1] Patent: WO2014/155264, 2014, A1,
[2] Patent: CN104030943, 2016, B,

[ 86123-95-7 ] Synthesis Path-Downstream 1~31

1
[ 3262-72-4 ]
[ 74-88-4 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In water; at 0 - 10℃; for 6h;	The above prepared compound of formula I (20.5g, 0 . 100mol) cooling the aqueous solution to 0-10C, maintain 0-10C, drop at the same time add iodomethane (28.4g, 0 . 20mol) and 50% sodium hydroxide (36.0g, 0 . 450mol), reaction mixture in 0-10 C reaction 6 hours, after the reaction, the reaction liquid maintain 0-10C, with 50% citric acid dyeworks to pH= 2-3, then with dichloromethane (1×123 ml, 2×82 ml) extraction and drying with anhydrous sodium sulfate, then distilled under reduced pressure to dry obtains the type compound II 21.9g (yield 100%, chiral purity 98.5%).
		Preparation of (R)-2-((tert-butoxy)carbonylamino)-3-methoxypropanoic acidTetrahydrofuran (350 ml), sodium hydride (40 gm) and imidazole (5 gm) were added and then cooled to 0 to 5C. To the reaction mixture was added a solution N-Boc- D-serine (100 gm) in tetrahydrofuran (900 ml) for 30 minutes and then maintained for 30 minutes at 0 to 5C. Methyl iodide (85 gm) was added to the reaction mixture and then maintained for 30 minutes. The temperature of the reaction mass was raised to room temperature and maintained for 2 hours. To the reaction mass was added methanol (50 ml) and then concentrated to obtain a residual mass. To the residual mass was added water (1000 ml) and then the layers were separated. The pH of the aqueous layer was adjusted to 2.8 with aqueous citric acid (50%) and extracted with methylene chloride. Then concentrated to obtain a residual solid of (R)-2-((tert-butoxy)carbonylamino)-3- methoxypropanoic acid (75 gm).

Reference： [1]Patent: CN104030943,2016,B .Location in patent: Paragraph 0140; 0141
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5817 - 5822
[3]Patent: WO2012/46245,2012,A1 .Location in patent: Page/Page column 8

2
[ 482308-10-1 ]
[ 86123-95-7 ]
[ 811450-77-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5817 - 5822

3
[ 482308-09-8 ]
[ 86123-95-7 ]
{1-[3-chloro-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-2-methoxy-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5817 - 5822

4
[ 86123-95-7 ]
4-(4-amino-2-fluorophenyl)morpholin-3-one [ No CAS ]
{1-[3-fluoro-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-2-methoxy-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5817 - 5822

5
[ 86123-95-7 ]
[ 482308-08-7 ]
{2-methoxy-1-[4-(3-oxo-morpholin-4-yl)-3-trifluoromethyl-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5817 - 5822

6
[ 862372-14-3 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		Methyl N-(tert-butoxycarbonyl)-O-methyl-D-serinate (2.0 g, 85. 7 mmol) was dissolved in tetrahydrofuran (40 ml) and water (20 ml) and lithium hydroxide mono hydrate (1. 8 g, 42.9 mmol) added. The mixture was stirred for 4 hours at room temperature, concentrated under reduced pressure to remove most of the tetrahydrofuran and then acidified by the addition of concentrated hydrochloric acid. The solution was extracted with ethyl acetate (three times). The combined organics were dried (MgS04), filtered and evaporated under reduced pressure to give N-(tert-butoxycarbonyl)-O-methyl-D-serine (1.9 g, 100%) as a colourless oil; IH NMR spectrum : (DMSO d6) 1.37 (s, 9H), 3.23 (s, 3H), 3.53 (m, 2H), 4. 18 (m, 1H), 6.87 (d, 1H), 12.60 (brs, 1H).

Reference： [1]Patent: WO2005/75439,2005,A1 .Location in patent: Page/Page column 127

7
[ 74-88-4 ]
[ 86123-95-7 ]

Reference： [1]Patent: WO2005/111029,2005,A1 .Location in patent: Page/Page column 168-169

8
[ 325125-06-2 ]
[ 86123-95-7 ]
[ 869859-79-0 ]

Reference： [1]Patent: WO2005/111014,2005,A1 .Location in patent: Page/Page column 134

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran; hexane;Purification / work up;	The <strong>[86123-95-7](R)-2-N-Boc-amino-3-methoxypropanoic acid</strong> (C-936) solution prepared in example 1 was evaporated in vacuo yielding (R)-2-N-Boc-amino-3- methoxypropanoic acid (C-936) as a waxy solid (23.7g, 100%). HPLC purity o 90.0%. Elemental analysis Calculated for C9Hi7NO5 49.31% C; 7.82% H; 6.39% N. Found 49.12% C; 7.72% H; 8.97% N.

10
[ 86123-95-7 ]
O-methyl-N-(tert-butoxycarbonyl)-D-serine hydroxamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With hydroxylamine hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; for 1 - 5h;pH 4.5 - 5.0;	To a THF (2 mL/1 mmol of amino acid) solution of the BOC-amino acid (1 equiv) was added a solution of hydroxylamine hydrochloride (2 equiv) in a H2O (4 mL/lmmol of hydroxylamine). The pH was maintained at 4.5-5. 0 while a THF (3mL/1 mmol OF DCC) solution of DCC (2 equiv) was added with stirring (1-5 h). The solid was filtered and the filtrate was concentrated in vacuo. The residue was purified by PTLC (EtOAc/hexanes) to afford the desired hydroxamic acid.

Reference： [1]Patent: WO2005/20973,2005,A2 .Location in patent: Page/Page column 24

11
[ 67-56-1 ]
[ 3262-72-4 ]
[ 74-88-4 ]
[ 86123-95-7 ]

Reference： [1]Patent: WO2005/111014,2005,A1 .Location in patent: Page/Page column 132-133

12
[ 3262-72-4 ]
[ 77-78-1 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		A solution of N-Boc-D-serine (22g, 0.107 mol) in dry tetrahydrofuran (352ml) was cooled to <-10C under a nitrogen atmosphere. To this was added via a dry addition funnel 15% w/w n-butyllithium in hexanes (134ml, 0.216mol) keeping the temperature <10C. The resultant slurry was aged for 1 hour at 0- 5C. Dimethyl sulphate (12.1ml, 0.128mol) was added keeping the temperature at 0-5C and the reaction mixture aged at 0-5C for 9 hours. The reaction was quenched by the addition of water (110ml), basified to pH 10-13 with 30% sodium hydroxide (3ml) and the tetrahydrofuran/hexane evaporated in vacuo. The residue was washed with toluene (44ml) and then acidified to a pH of <3.5 with 50% citric acid. The acidified aqueous phase was extracted with methylene chloride (2x91 ml, 1x66ml) and the combined C936 extracts dried by azeotropic distillation. Yield on evaporation 23.7g, 100%. HPLC purity 90.0%, Chiral purity 100%.
100%		A suspension of N-Boc-D-serine (22g, 0.107 mol) and tetrabutylammonium bromide (1.3g, 0.004mol) in toluene (110ml) was cooled to <10C. To this was added 20% sodium hydroxide (17.6ml, 0.107mol) keeping the temperature <10C and the resultant mixture was aged for 30 minutes at <10C. Dimethyl sulphate (40.6ml, 0.429mol) and 50% sodium hydroxide (25.4ml, 0.485mol) were added keeping the temperature <10C and the reaction mixture aged at 10C for 1 hour. Water (66ml) was added to the mixture and the phases separated. The aqueous layer was acidified to a pH of <3.5 with 50% citric acid, extracted with methylene chloride (2x91 ml, 1x66ml) and the combined C936 extracts dried by azeotropic distillation. (Yield on evaporation 27.5g, 100%, HPLC purity 96.3%, Chiral purity 98.1%).
100%	With sodium hydroxide; In water; at 0 - 10℃; for 6h;	The above prepared compound of formula I (20.5g, 0 . 100mol) cooling the aqueous solution to 0-10C. Maintain 0-10C, at the same time by adding drops of sulfuric acid dimethyl ester (50.5g, 0 . 400mol) and 50% sodium hydroxide (36.0g, 0 . 450mol), reaction mixture in 0-10 C reaction 6 hours. After the reaction, the reaction liquid maintain 0-10C, with 50% citric acid dyeworks to pH= 2-3, then with dichloromethane (1×123 ml, 2×82 ml) to extract and after drying with anhydrous sodium sulfate is distilled under reduced pressure to dry obtains the type compound II 21.9g (yield 100%, HPLC purity 92.9%, chiral purity 98.0%).

83%		Synthesis of (R)-2-N-Boc-amino-3-methoxypropanoic acid[0155] A suspension of N-Boc-D-serine (17.6 g, 86 mmol) and tetrabutylammonium bromide (1.04 g, 3.23 mmol) in toluene (90 mL) was cooled with an ice-bath with stirring. To the reaction mixture was added 20% sodium hydroxide (14 mL, 86 mmol) and the resulting mixture was stirred for thirty minutes. Dimethyl sulphate (43.3 g, 343 mmol) and 50% sodium hydroxide (20.3 mL, 388 mmol) were added and the reaction mixture was stirred at < 10 C for 3 hours. Water (60 ml) was then added to the mixture and the resulting two phases were separated. The aqueous phase was washed with dichloromethane (100 mL x 2). The aqueous phase was then acidified to a pH of <3.5 with 50% citric acid and extracted with methylene chloride (100 mL chi 3). The organic phases were combined, dried over sodium sulfate, filtered, and solvent removed under reduced pressure to afford a colorless oil (15.6 g, yield: 83%, purity >95%). 1H NMR (500 MHz, CDC13) delta 1.45 (s, 9H), 3.37 (s, 3H), 3.62 (m, 1H), 3.85 (m, 1H), 4.43 (m, 1H), 5.42 (d, 1H). LC-MS (m/z) calculated 219.1 , found 242.0 [M + Naf.
	With sodium hydroxide; In water; at 0 - 5℃;	Example 1:Preparation of N-Boc-O-methyl-D-serine: Into a 2L, four-necked RB flask was charged 90 ml of water and 40 g of sodium hydroxide. D-Serine is added to the solution at 20-25 C. Boc anhydride (150 g) is slowly added to the reaction mass keeping the temperature below 20C. The reaction mass was allowed to reach 25-30C and maintained for 16 h. TLC of the reaction mass showed the presence of D-serine content at <1.0% level. The reaction mass is cooled to 0-5C and started the simultaneous addition of aqueous sodium hydroxide (104 g of sodium hydroxide dissolved in 100 ml of water) and dimethyl sulphate (300 g) through addition funnels keeping the temperature below 5C. The reaction mass was maintained at same temperature till the completion of reaction. The reaction mass is diluted with water and extracted the product into diisopropyl ether. Aqueous layer is neutralized with citric acid to get < 3.5 pH. The reaction mass is extracted with diisopropyl ether and distilled of solvent to get 87 g of title compound as an oil.
		Example-31: Preparation of (R)-2-(fc/*/-butoxycarbonylamino)-3-methoxy propionic acid compound of formula- 17:; Sodium hydroxide (19 g) was added to a reaction mixture containing N-Boc-D-serine (430 ml) obtained in example-30 at 0-5C and stirred for 30 mins. Dimethylsulphate (340 ml) and sodium hydroxide solution (153 g in 152 ml of water) was added reaction mixture slowly over 4 hours at 5-10C and then stirred for 10 hrs. The pH of the reaction mass was acidified with dilute hydrochloric acid at 0-5C. Methylene chloride (100 ml) was added to the reaction mixture and the layers get separated. Aqueous layer was extracted with methylene chloride and the methylene chloride layer containing the title compound was directly used for the next stage without anyv purification.
		Preparation of (R)-2-((tert-butoxy)carbonylamino)-3-methoxypropanoic acid N-Boc-D-serine (95 gm) as obtained example 1, methylene chloride (380 ml) and tetra-butyl ammonium bromide (1 gm) were added and then cooled to 0 to 5C. To the reaction mixture was added caustic soda lye (48%, 123 gm) and then maintained for 30 minutes at 0 to 5C. Dimethyl sulphate (121 gm) was added to the reaction mixture and then maintained for 30 minutes. The temperature of the reaction mass was raised to room temperature and then maintained for 3 hours at room temperature. To the reaction mass was added water (300 ml) and then the layers were separated. The pH of the aqueous layer was adjusted to pH is 2.8 with aqueous citric acid (50%) and extracted with methylene chloride. The solvent was distilled off to obtain a residual solid of (R)-2- ((tert-butoxy)carbonylamino)-3-methoxypropanoic acid (92.5 gm).
87 g	With sodium hydroxide; In water; at 0 - 5℃;	Into a 2 L, four-necked RB flask was charged 90 ml of water and 40 g of sodium hydroxide. D-Serine is added to the solution at 20-25 C. Boc anhydride (150 g) is slowly added to the reaction mass keeping the temperature below 20 C. The reaction mass was allowed to reach 25-30 C. and maintained for 16 h. TLC of the reaction mass showed the presence of D-serine content at <1.0% level. The reaction mass is cooled to 0-5 C. and started the simultaneous addition of aqueous sodium hydroxide (104 g of sodium hydroxide dissolved in 100 ml of water) and dimethyl sulphate (300 g) through addition funnels keeping the temperature below 5 C. The reaction mass was maintained at same temperature till the completion of reaction. The reaction mass is diluted with water and extracted the product into diisopropyl ether. Aqueous layer is neutralized with citric acid to get <3.5 pH. The reaction mass is extracted with diisopropyl ether and distilled of solvent to get 87 g of title compound as an oil.
34.5 g	With sodium hydroxide; In water; at 5 - 10℃; for 14h;	To a stirred aqueous solution of sodium hydroxide (23.1 g of NaOH in 150 ml of water) was added D-serine (30 g) lot wise at 2G-25C and BOC anhydride (74.7 g) at 10-15C. The traction mixture was stirred at 20-25 0C for 10 hours. Sodium hydroxide pellets (11.4g) was added to the reaction mixture at 5-10C and stirred for another 30 mins. To the resulting reaction mixture was slowly added dimethylsulphate (340 ml) and aqueous solution of sodium hydroxide (91.0 g NaOH in 1 10 mL of water) at 5-10C over 4 hours and then stirred for 10 hrs. The reaction mixture was acidified to pH -1 -2 with 2% hydrochloric acid solution at 0-5C and extracted with methylene chloride (300 ml). Separating organic layer, aqueous layer was extracted with methylene chloride (100 mL). The combined organic layer was concentrated under vacuum. The obtained residue was dissolved in methyl tert-butyl ether (83.25 mL) at 60-65C. To the resulting solution was added H-hexane (466.2 mL) at 20-25C and mixture was stirred for 10-12h. The solid was filtered and dried to provide the title compound as white solid. Weight: 34.5 g Yield: 55.29%.

Reference： [1]Patent: WO2006/37574,2006,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2006/37574,2006,A1 .Location in patent: Page/Page column 17-18
[3]Patent: CN104030943,2016,B .Location in patent: Paragraph 0103; 0104
[4]Patent: WO2012/51551,2012,A1 .Location in patent: Page/Page column 36-37
[5]Tetrahedron,2010,vol. 66,p. 5384 - 5395
[6]Patent: WO2011/95995,2011,A1 .Location in patent: Page/Page column 10-11
[7]Patent: WO2011/99033,2011,A1 .Location in patent: Page/Page column 42
[8]Patent: WO2012/46245,2012,A1 .Location in patent: Page/Page column 7-8
[9]Patent: US2013/35508,2013,A1 .Location in patent: Paragraph 0031
[10]Patent: WO2014/155264,2014,A1 .Location in patent: Page/Page column 11-12

13
[ 2133-40-6 ]
[ 86123-95-7 ]
[ 1239920-13-8 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 5384 - 5395

14
[ 100-46-9 ]
[ 86123-95-7 ]
[ 880468-89-3 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a solution of acid (R)-9 (0.7 g, 3.2 mmol) in dry THF was added N-methylmorpholine (0.43 mL, 3.8 mmol) at -78 °C under an argon atmosphere. After 5 min, isobutyl chloroformate (0.5 mL, 3.8 mmol) was added and stirred for another 5 min. To this reaction mixture benzylamine (0.4 mL, 3.8 mmol) was added at -78 °C after which the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was filtered, and washed with ethylacetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, petroleum ether/acetone, 85:15) to yield (R)-10 as a colorless solid (0.9 g, 90percent); mp 63-64 °C; (c 0.9, CHCl3); IR (CHCl3, cm-1): numax 3683, 3431, 3020, 2931, 2401, 1714, 1523, 1496, 1368, 1165, 1119, 928, 758, 669; 1H NMR (200 MHz, CDCl3): deltaH 1.43 (s, 9H), 3.37 (s, 3H), 3.47-3.54 (dd, J = 9.2, 6.1 Hz, 1H), 3.82 (dd, J = 9.3, 3.7 Hz, 1H), 4.27 (m, 1H), 4.47 (d, J = 5.1 Hz, 1H), 5.41 (br s, 1H), 6.77 (m, 1H), 7.22-7.37 (m, 5H); 13C NMR (50 MHz, CDCl3): deltaC 170.3 (CO), 155.5 (CO), 137.9 (C), 128.7 (CH, 2 carbons), 127.5 (CH, 3 carbons), 80.4 (C), 72.1 (CH2), 59.1 (CH3), 54.0 (CH), 43.5 (CH2), 28.3 (CH3, 3 carbons); MS: m/z 331 [M+Na]+.
90%	With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -78 - 30℃; for 1h;Inert atmosphere;	Example-5 Synthesis of (R)-tert-butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate (R)-9 To a solution of acid (R)-8 (0.7 g, 3.2 mmol) in dry THF was added N-methylmorpholine (0.43 mL, 3.8 mmol) at -78° C. under argon atmosphere. After 5 min, isobutyl chloroformate (0.5 mL, 3.8 mmol) was added and stirred the content for another 5 min. To this reaction mixture benzylamine (0.4 mL, 3.8 mmol) was added at -78° C. and allowed the reaction mixture to stir at 30° C. for 1 h. After completion of the reaction, reaction mixture was filtered, washed with ethylacetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, petroleum ether/acetone, 85:15) to yield (R)-9 as colorless solid (0.9 g, 90percent). m.p 63-64° C.; [alpha]25D=-20.5 (c 0.9, CHCl3); IR (CHCl3, cm-1): vmax 3683, 3431, 3020, 2931, 2401, 1714, 1523, 1496, 1368, 1165, 1119, 928, 758, 669; 1H NMR (200 MHz, CDCl3): deltaH 1.43 (s, 9H), 3.37 (s, 3H), 3.47-3.54 (dd, J=9.2, 6.1 Hz, 1H), 3.82 (dd, J=9.3, 3.7 Hz, 1H), 4.27 (m, 1H), 4.47 (d, J=5.1 Hz, 1H), 5.41 (bs, 1H), 6.77 (m, 1H), 7.22-7.37 (m, 5H); 13C NMR (50 MHz, CDCl3): deltaC 170.3 (CO), 155.5 (CO), 137.9 (C), 128.7 (CH, 2 carbons), 127.5 (CH, 3 carbons), 80.4 (C), 72.1 (CH2), 59.1 (CH3), 54.0 (CH), 43.5 (CH2), 28.3 (CH3, 3 carbons); MS: m/z 331 [M+Na]+.
90%		To a solution of acid 5 (0.985 g, 4.49 mmol) in dry THF (10ml) was added N-methylmorpholine (0.6 mL, 5.39 mmol) at -78 °C under an argon atmosphere.After 5 min, isobutyl chloroformate (0.7 mL, 5.39 mmol)was added and stirred for another 5 min. To this reaction mixture benzyl amine (0.6 mL, 5.39 mmol) was added at -78 °C andthe reaction mixture was allowed to come up to room temperature and stirred foranother 1 h. After completion of the reaction (TLC), the reaction mixture wasfiltered through a pad of celite, and washed with ethyl acetate (20 mL). Thesolvent was removed under reduced pressure and the crude reaction mixture wassubjected to flash chromatography (CombiFlash Rf 200i, Teledyne Isco) using RediSep silica gel column (12 g) eluting with petroleum ether?EtOAc (3:2,isocratic) to yield 6as a white solid (1.24 g, 90percent); Rf0.35 (40percent EtOAc inpetroleum ether); mp 63-64 °C [Lit.63-64 °C3]; [alpha]D26 -24.3 (c 1.04, CHCl3) [Lit. [alpha]D26-20.5 (c 0.9, CHCl3)3]; IR (CHCl3) umax:3428, 3345, 3017, 2933, 2405, 1708, 1671, 1493, 1365, 1220, 1167, 1116, 1075,1025, 922, 860, 762, 668 cm-1; 1H NMR (200 MHz, CDCl3) delta: 7.40-7.19 (m, 5H), 6.78 (brs, 1H),5.55-5.33 (m, 1H), 4.48 (d, J = 4.3 Hz, 2H), 4.27 (brs, 1H), 3.84 (dd, J= 3.9, 9.2 Hz, 1H), 3.50 (dd, J = 6.2, 9.1 Hz, 1H), 3.36 (s, 3H), 1.43(s, 9H); 13C NMR (50 MHz,CDCl3) delta: 170.3,155.5, 138.0, 128.7, 127.5, 80.4, 72.1, 59.1, 43.5, 28.3; HRMS (ESI): m/z calcdfor C16H24N2O4Na [M + Na]+331.1628; found: 331.1612.

46.4%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h;Cooling with ice;	Synthesis of (R)-N-Benzyl-2-Boc-amino-3-methoxypropionamide[0157] <strong>[86123-95-7](R)-2-N-Boc-amino-3-methoxypropanoic acid</strong> (15.0 g, 68.4 mmol), phenylmethanamine (7.33 g, 68.4 mmol), and DMAP (4.17 g, 34.2 mmol) were dissolved in DCM (150 mL). The solution was cooled in an ice-bath and EDC (21 .21 g, 137 mmol) was added dropwise to the solution. Once addition was complete, the reaction mixture stirred at warmed to room temperature and stirred for two hours. Then DCM (200 ml) was added to the mixture. The DCM organic phase was washed with H20 (200 mL x 1 ), 0.5 N HC1 (200 mL x 2), 5percent sodium bicarbonate (200 mL chi 2) and water (200 mL x 2). The organic phase was dried over sodium sulfate, filtered, and solvent removed under reduced pressure. The desired product was obtained as a colorless semi-solid with a purity >95percent (9.8 g, 46.4percent). NMR (500 MHz, CDC13) delta 1.46 (s, 9H), 3.38 (s, 3H), 3.51 (m, 1H), 3.86 (d, 1 H), 4.30 (br., 1H), 4.50 (s, 2H), 5.42 (br., 1H), 6.74 (br., 1H), 7.28 (m, 3H), 7.35 (m, 2H). LC-MS (m/z) , calculated. 308.2, found 309.1 [M + H]+, 331.1 [M + Naf.
		The C936 solution prepared as above in example 2 was cooled to <-10°C and isobutyl chloroformate (14.2ml, 0.107mol) at <-5°C. N-methylmorpholine (11.8ml, 0.17mol) was added at<-5°C and the mixture aged for 30 minutes at <-5O. A solution of benzylamine (12.2ml, 0.11mol) in methylene chloride was added at <-5°C and the mixture warmed to room temperature. After aging for 1 hour the mixture was washed with water (44ml), 1N HCI (44ml), 8percent sodium bicarbonate (44ml) and water (44ml) to yield a C937 solution in methylene chloride.
		Example-32: Preparation of (R)-2-tert-butyl l-(benzylamino)-3-methoxy-l- oxopropan-2-yl carbonate compound of formuIa-18:; Ethylchoroformate (49.3 g) followed by N-methylmorpholine (46 g) was added to a pre-cooled reaction mass of (R)-2-(tert-butoxycarbonylamino)-3-methoxy propionic acid (280 ml) obtained in example-31 at -10 to -15°C and stirred for 15 min at -15°C. Benzylamine (49 g) was added to the reaction mixture slowly at -10 to -15 °C and stirred for 1.5 hours. Reaction temperature was raised to 20-25°C and stirred for 1.5 hours. The reaction mixture was washed with dilute hydrochloric acid (100 ml), and further the organic layer was washed with sodium bicarbonate solution followed by washed with water. The reaction mixture containing title compound was directly used for next stage without any isolation and purification.
		Preparation of (R)-N-benzyl-2-((tert-butoxy)carbonylamino)-3- methoxypropionamide(R)-2-((Tert-butoxy)carbonylamino)-3-methoxypropanoic acid (92.5 gm) as obtained in example 2 was dissolved in methylene chloride (925 ml) and then cooled to - 10°C. To the solution was added isobutyl chloroformate (57 ml) and then added 4- methylmorpholine (46.5 ml). The reaction mass was maintained for 30 minutes at -5°C and then added a solution of benzyl amine (46 ml) in methylene chloride (46 ml). The temperature of the reaction mass was raised to room temperature and then added water (140 ml). The separated organic layer was dried with sodium sulfate and the solvent was distilled off to obtain a residual mass. To the residual mass was added n-hexane (1200 ml) and stirred for 2 hours at room temperature. The solid obtained was collected by filtration and dried to obtain 116 gm of (R)-N-benzyl-2-((tert-butoxy)carbonylamino)-3- methoxypropionamide.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1353 - 1357
[2]Patent: US2014/12044,2014,A1 .Location in patent: Paragraph 0074; 0075
[3]Tetrahedron Letters,2015,vol. 56,p. 5802 - 5803
[4]Patent: WO2012/51551,2012,A1 .Location in patent: Page/Page column 36-37
[5]Patent: WO2006/37574,2006,A1 .Location in patent: Page/Page column 18
[6]Patent: WO2011/99033,2011,A1 .Location in patent: Page/Page column 42
[7]Patent: WO2012/46245,2012,A1 .Location in patent: Page/Page column 9

15
[ 76-05-1 ]
[ 86123-95-7 ]
[ 1318791-64-8 ]

Yield	Reaction Conditions	Operation in experiment
	In di-isopropyl ether; at 5 - 25℃;	Example 2:Preparation of O-methyl-D-serine trifluoroacetate salt: Into a 1L, four-necked, RB flask was charged 330 ml of diisopropyl ether and 78 g of <strong>[86123-95-7]N-Boc-O-methyl-D-serine</strong>. The reaction mass was cooled to <5C and added 400 g of trifluoroacetic acid. The reaction temperature was allowed to reach 25C and maintained for 20h. Solvent and excess trifluoroacetic acid was distilled of from the reaction mass under vacuum at 60C. The residue was crystallized from ethyl acetate/diisopropyl ether and filtered to get 50g of O-methyl-D-serine trifluoroacetate salt as white crystalline solid. M. R.: 228-230C. IR (KBr): 3415, 3133, 2980, 2932, 1726, 1680, 1646, 1560, 1425, 1366, 1256, 1210, 1 184, 1 125, 964, 842, 798, 726 and 514 cm'1. -NMR (400 MHz, DMSO-d6): 7.81 (broad s, exch. with D20, COOH and NH2), 3.79 (t, J = 4.4 Hz, 1H, CH), 3.66 (d, J = 4.8 Hz, 2H, CH2), 3.38 (s, 3H, OMe). I3C-NMR (100 MHz, DMSO-d6): 169.06, 158.29 (q, J = 31.3 Hz, CF3COOH), 1 17.20 (q, J = 297.6 Hz, CF3), 70.1 1 (OCH3), 58.50 (OCH2), 52.80 (CHCOOH). EI-MS: 121 (M + 2), 120 (M + 1), and 88 (M - OCH3).
50 g	In di-isopropyl ether; at 5 - 25℃; for 20h;	Into a 1 L, four-necked, RB flask was charged 330 ml of diisopropyl ether and 78 g of <strong>[86123-95-7]N-Boc-O-methyl-D-serine</strong>. The reaction mass was cooled to <5 C. and added 400 g of trifluoroacetic acid. The reaction temperature was allowed to reach 25 C. and maintained for 20 h. Solvent and excess trifluoroacetic acid was distilled of from the reaction mass under vacuum at 60 C. The residue was crystallized from ethyl acetate/diisopropyl ether and filtered to get 50 g of O-methyl-D-serine trifluoroacetate salt as white crystalline solid. M. R. 228-230 C. IR (KBr): 3415, 3133, 2980, 2932, 1726, 1680, 1646, 1560, 1425, 1366, 1256, 1210, 1184, 1125, 964, 842, 798, 726 and 514 cm-1. 1H-NMR (400 MHz, DMSO-d6): 7.81 (broad s, exch. with D2O, COOH and NH2), 3.79 (t, J=4.4 Hz, 1H, CH), 3.66 (d, J=4.8 Hz, 2H, CH2), 3.38 (s, 3H, OMe). 13C-NMR (100 MHz, DMSO-d6): 169.06, 158.29 (q, J=31.3 Hz, CF3COOH), 117.20 (q, J=297.6 Hz, CF3), 70.11 (OCH3), 58.50 (OCH2), 52.80 (CHCOOH): EI-MS: 121 (M+2), 120 (M+1), and 88 (M-OCH3).

Reference： [1]Patent: WO2011/95995,2011,A1 .Location in patent: Page/Page column 11
[2]Patent: US2013/35508,2013,A1 .Location in patent: Paragraph 0032

16
[ 24424-99-5 ]
[ 86123-95-7 ]

Reference： [1]Patent: WO2011/99033,2011,A1
[2]Patent: WO2012/46245,2012,A1
[3]Patent: WO2012/46245,2012,A1
[4]Patent: WO2014/155264,2014,A1
[5]Patent: CN104030943,2016,B
[6]Patent: CN104030943,2016,B

17
tert-butyl [(2R)-1-hydroxy-3-methoxypropan-2-yl]carbamate [ No CAS ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hypochlorite; sodium chlorite; potassium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 20℃; for 3h;	To a solution of compound 4 (0.920 g, 4.48 mmol) in CH3CN (4.6 mL) and saturatedsolution of KH2PO4 (4.6 mL) were added NaClO2(0.810 g, 8.96 mmol), TEMPO (0.190 g, 1.21 mmol) and NaOCl (0.19 mL). Afterstirring for 3 h, the mixture was poured into water (9 mL) and extracted withdichloromethane (3 X 30 mL). The combined organic extracts were washed withwater, brine and dried over anhydrous Na2SO4. Afterevaporation of the solvent, the product 5was used in the next step without further purification (0.985 g, 99%); lightorange liquid; Rf0.16 (60% EtOAc in petroleum ether); [alpha]D26-13.4 (c 1.03, CHCl3) [Lit. [alpha]D26-19.2 (c 1.4, CHCl3)3]; IR (CHCl3) umax:3441, 3018, 2985, 2935, 1713, 1505, 1405, 1376, 1218, 1166, 1118, 1063, 925,850, 762, 669 cm-1; 1H NMR (200 MHz, CDCl3) delta: 5.43 (brs, 1H), 4.42 (brs, 1H), 3.85 (d, J = 8.5 Hz, 1H),3.64 (d, J = 7.3 Hz, 1H), 3.37 (s, 3H), 1.45 (s, 9H); 13CNMR (50 MHz, CDCl3) delta: 174.8, 155.8, 80.3, 72.5, 59.4, 28.4;HRMS (ESI): m/z calcdfor C9H17NO5Na [M + Na]+ 242.0999; found: 242.0987.
83%	With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 35℃; for 6h;pH 6.7;aq. phosphate buffer;	A mixture of (S)-8 (1 g, 4.9 mmol), TEMPO (0.05 g, 0.32 mmol), acetonitrile (20 mL), and sodium phosphate buffer (16 mL, 0.67 M, pH 6.7) was heated to 35 C. Next, sodium chlorite (1.32 g dissolved in 2 mL water, 14.6 mmol) and diluted bleach (4-6%, 1 mL diluted in 2 mL water) were added simultaneously over 1 h. The reaction mixture was stirred at 35 C until the reaction was complete (6 h, TLC), then cooled to room temperature. Water (30 mL) was added and the pH adjusted to 8 with 2 M NaOH. The reaction was quenched by pouring it into an ice cold Na2SO3 solution maintained at <20 C. After stirring for 30 min at room temperature, ethylacetate (30 mL) was added and the stirring continued for an additional 15 min. The organic layer was separated and discarded. More ethylacetate (30 mL) was added, and the aqueous layer was acidified with M HCl to pH 3-4. The organic layer was separated, washed with water (2 × 15 mL), brine (20 mL) and concentrated under reduced pressure to afford the carboxylic acid (R)-9 (0.88 g, 83%); (c 1.4, CHCl3); IR (CHCl3, cm-1): numax 3443, 3019, 2982, 2932, 1708, 1501, 1393, 1369, 1216, 1164, 1119, 1064, 927, 757, 669; 1H NMR (200 MHz, CDCl3): deltaH 1.46 (s, 9H), 3.38 (s, 3H), 3.59-3.66 (dd, J = 9.4, 3.7 Hz, 1H), 3.84-3.90 (dd, J = 9.6, 3.1 Hz, 1H), 4.41-4.47 (m, 1H), 5.42 (d, J = 8.2 Hz, 1H) 8.16 (br s, 1H); 13C NMR (50 MHz, CDCl3): deltaC 175.4 (CO), 155.8 (CO), 80.3 (C), 72.1 (CH2), 59.3 (CH), 53.7 (CH3), 28.3 (CH3, 3 carbons); MS: m/z 242 [M+Na]+.
83%	With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; acetonitrile; at 35℃; for 7h;pH 6.7;	Example-4 Synthesis of (R)-2-(tert-butoxycarbonylamino)-3-methoxypropanoic Acid (R)-8 A mixture of (S)-7 (1 g, 4.9 mmol), TEMPO (0.05 g, 0.32 mmol), acetonitrile (20 mL), and sodium phosphate buffer (16 mL, 0.67 M, pH 6.7) was heated to 35 C. Then sodium chlorite (1.32 g dissolved in 2 mL water, 14.6 mmol) and dilute bleach (4-6%, 1 mL diluted in 2 mL water) were added simultaneously over 1 h. The reaction mixture was stirred at 35 C. until the reaction is complete (6 h, TLC), then cooled to room temperature. Water (30 mL) was added and the pH was adjusted to 8 with 2 N NaOH. The reaction was quenched by pouring into ice cold Na2SO3 solution maintained at <20 C. After stirring for 30 min at 30 C. ethylacetate (30 mL) was added and continued the stirring for additional 15 min. The organic layer was separated and discarded. More ethylacetate (30 mL) was added, and the aqueous layer was acidified with 2N HCl to pH 3. The organic layer was separated, washed with water (2*15 mL), brine (20 mL) and concentrated under reduced pressure to afford the carboxylic acid (R)-8 (0.88 g, 83%). [alpha]25D=-19.2 (c 1.4, CHCl3); IR (CHCl3, cm-1): vmax 3443, 3019, 2982, 2932, 1708, 1501, 1393, 1369, 1216, 1164, 1119, 1064, 927, 757, 669; 1H NMR (200 MHz, CDCl3): deltaH 1.46 (s, 9H), 3.38 (s, 3H), 3.59-3.66 (dd, J=9.4, 3.7 Hz, 1H), 3.84-3.90 (dd, J=9.6, 3.1 Hz, 1H), 4.41-4.47 (m, 1H), 5.42 (d, J=8.2 Hz, 1H) 8.16 (bs, 1H); 13C NMR (50 MHz, CDCl3): deltaC 175.4 (CO), 155.8 (CO), 80.3 (C), 72.1 (CH2), 59.3 (CH), 53.7 (CH3), 28.3 (CH3, 3 carbons); MS: m/z 242 [M+Na]+.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5802 - 5803
[2]Tetrahedron Asymmetry,2011,vol. 22,p. 1353 - 1357
[3]Patent: US2014/12044,2014,A1 .Location in patent: Paragraph 0072; 0073

18
[ 86123-95-7 ]
lacosamide [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1353 - 1357
[2]Patent: US2014/12044,2014,A1

19
[ 86123-95-7 ]
[ 1374969-20-6 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[86123-95-7]N-Boc-O-methyl-D-serine</strong> (438 mg, 2.00 mmol), HOBt monohydrate (364 mg, 2.38 mmol) and EDC (460 mg, 2.39 mmol) in DMF (9 mL) was stirred at room temperature for 2 h, cone. NH4OH (0.700 mL, ca. 9.80 mmol) was added. The mixture was stirred for 18 h. Water and EtOAc were added. The organic phase was washed with 5% NaHC03, dried over Na2S04, concentrated in vacuo to give (R)-tert-butyl l-amino-3- methoxy-l-oxopropan-2-ylcarbamate (100 mg). The aqueous phase was further extracted with nBuOH (30 mL). The nBuOH solution was washed with 5% NaHC03, then was concentrated in vacuo to give another portion of (R)-tert-butyl l-amino-3-methoxy-l- oxopropan-2-ylcarbamate (242 mg).

Reference： [1]Patent: WO2012/61418,2012,A2 .Location in patent: Page/Page column 108-109
[2]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6828 - 6831,4

20
[ 86123-95-7 ]
(R)-tert-butyl (1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)-N-(hydroxymethyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2014/155264,2014,A1

21
[ 86123-95-7 ]
[ 880468-89-3 ]

Reference： [1]Patent: WO2014/155264,2014,A1
[2]Patent: CN104030943,2016,B

22
[ 50-00-0 ]
[ 86123-95-7 ]
(4R)-3-(tert-butyloxycarbonyl)-4-(methoxymethyl)-5-oxazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.19%	With toluene-4-sulfonic acid; In toluene; at 120 - 130℃;Dean-Stark;	The solution of N-Boc O-methyl Serine ( 1.0 g) in toluene ( 10 mL), para toluene suiphonic acid (0.086 g) and formalin (0.74 g) was charged into a round bottom flaskfitted with dean-stark, thermometer and stirred at 120-130C for 3-4h. To cooled solution activated charcoal (0.2 g), hyfio (1.0 g) and aqueous sodium hydrogen carbonate solution (5 mL) was added to it and stirred for 30 min. The reaction mixture was filtered through hyflo and separated organic layer was washed with water (2x5 mL) and concentrated under reduce pressure to yield title compound (0.8 g, 76.19%).

Reference： [1]Patent: WO2014/155264,2014,A1 .Location in patent: Page/Page column 12-13

23
[ 721928-19-4 ]
[ 86123-95-7 ]

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5802 - 5803

24
[ 108149-63-9 ]
[ 86123-95-7 ]

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5802 - 5803

25
3-azaspiro[5.5]undecan-2,4-dioxo-3-yl diphenyl phosphate [ No CAS ]
[ 86123-95-7 ]
2,4-dioxo-3-azaspiro[5.5]undecan-3-yl N-(tert-butoxycarbonyl)-O-methyl-D-serinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.3%		To a solution of N-(tert-butoxycarbonyl)-O-methyl-d-serine Ia, (Scheme 5) (5.0g, 22.8mmol) in dichloromethane (25mL) was added triethyl amine (2.54g, 25.1mmol) and the reaction mixture was stirred under an N2 atmosphere. After 10min, ASUD-Di phenyl phosphate (10.8g, 25.1mmol) was added and the reaction mixture was stirred at ambient temperature for 5h. After completion of the reaction, the reaction mixture was washed with water (15ml), brine (15mL), dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/ethyl acetate, 80:20) to afford 2,4-dioxo-3-azaspiro[5.5]undecan-3-yl N-(tert-butoxycarbonyl)-O-methyl-d-serinate Ib as a colorless oil (8.3g, 91.3%); 98.37% purity by HPLC (Method d, Table 1);% ee: 99.21% (Method j, Table 1) (d-isomer Rt=11.89min; l-isomer Rt=14.74min); IR (CHCl3, cm-1): vmax 3441, 3019, 2980, 2933, 2859, 1812, 1750, 1715, 1502, 1455, 1393, 1368, 1342, 1282, 1244, 1215, 1196, 1170, 1135, 1116, 1107, 1064, 966, 926, 878, 851, 758, 668; 1H NMR (300MHz, CDCl3): deltaH 1.45-1.59 (m, 19H), 2.60-2.69 (m, 2H), 2.76-2.82 (m, 2H), 3.42 (s, 3H), 3.74-3.78 (dd, J=9.6, 3.6 HZ, 1H), 3.86-3.91, J=9.6, 3.6 HZ, 1H), 4.82 (m, 1H), 5.37 (d, 1H); 13C NMR (75MHz, CDCl3): deltaC 167.5, 165.5, 154.8, 80.2, 72.0, 59.2, 52.3, 44.1, 36.6, 35.0, 32.6, 28.2, 25.5, 21.4; MS: m/z 398.58 [M]+, 415.79 [M+H2O]+, 420.9 [M+Na]+.

Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 487 - 491

26
[ 3282-30-2 ]
[ 86123-95-7 ]
N-Boc-O-methyl-D-serine pivalic anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In dichloromethane; at 0 - 5℃; for 1h;	The above prepared compound of formula II (21.9g, 0 . 100mol) dissolved in dichloromethane (110 ml), cooled to 0 C, and in 0-5 C added pivaloyl chloride (12.6g, 0 . 100mol), in 0-5 C adding N-methyl morpholine (11.1g, 0 . 110mol) and in 0-5 C reaction 1 hour, the dichloromethane solution of compound III obtains the type, the dichloromethane solution of the compound of formula III without processing, directly used for the next step synthesis.

Reference： [1]Patent: CN104030943,2016,B .Location in patent: Paragraph 0112; 0113

27
[ 67-56-1 ]
[ 86123-95-7 ]
methyl (2R)-2-amino-3-methoxypropanoate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.2%	With thionyl chloride; at 0 - 20℃; for 2h;	42.9 g of Compound II was dissolved in 400 mL of anhydrous methanol,Cooled to 0-5 C,Thionyl chloride was added dropwise at this temperature 50g,The reaction was stirred for 2 hours until the temperature reached to room temperature.Some solvents were distilled off under reduced pressure,When the remaining amount is 50 g,Under stirring, dry ethyl acetate (400 mL) was added.After stirring for 30 minutes,filter,The filtrate was concentrated to dryness under reduced pressure,32.5g of white solid was obtained.Yield: 89.2%, HPLC purity: 98.2%.

Reference： [1]Patent: CN106699595,2017,A .Location in patent: Paragraph 0038; 0039

28
[ 3262-72-4 ]
[ 80-48-8 ]
[ 86123-95-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		In a 1000 mL three-necked flask,400 mL of toluene and 40 g of N-tert-butoxycarbonyl-D-serine (Boc-D-serine)The stirring temperature was lowered to 0-5 C,36.5 g of 30% potassium hydroxide solution was added dropwise.After stirring for 30 minutes,Then 72.65 g of methyl p-toluenesulfonate was added,Tetrabutylammonium bromide 4g,Then 43.68 g of 50% potassium hydroxide solution was added dropwise.After reaction at 0-5 C for 8 hours,Add water 200mL and layered,The aqueous layer was washed with 100 mL of toluene,Discard the organic layer.The combined aqueous layers were then cooled to below 15 [deg.] C and acidified with 50% phosphoric acid to pH = 2-3.5,Extraction with dichloromethane (200 mL * 3)The combined organic layers were added 30g of anhydrous sodium sulfate and stirred overnight.The next day filterThe filtrate was concentrated to dryness under reduced pressure,42.9 g of light yellow oil,Yield: 100%, HPLC purity: 98.0%, Chiral purity: 99.4%.

Reference： [1]Patent: CN106699595,2017,A .Location in patent: Paragraph 0036; 0037

29
[ 1117-97-1 ]
[ 86123-95-7 ]
[ 477940-53-7 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g		1,1'-carbonyldiimidazole (1.9 g) was added to a dichloromethane solution (10 ml) containing <strong>[86123-95-7](R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid</strong> (2 g) in an ice bath, followed by stirring for 30 minutes. Subsequently, triethylamine (1.2 g) and N,O-dimethylhydroxylamine (1.2 g) were added, followed by stirring at room temperature for 2.5 hours. The reaction solution was added dropwise to 4M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and water and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, and yellow oily matter of (R)-tert-butyl(1-(methoxy(methyl)amino)-1-oxobutan-2-yl)carbamate (1.8 g) was thus obtained. MS (ESI m/z): 263 (M+H) RT (min): 1.03

Reference： [1]Patent: EP2589592,2018,B1 .Location in patent: Paragraph 1306; 1307

30
[ 3262-72-4 ]
[ 77-78-1 ]
[ 862372-15-4 ]
[ 86123-95-7 ]

Reference： [1]Organic Process Research and Development,2019,vol. 23,p. 818 - 824

31
[ 100-46-9 ]
[ 86123-95-7 ]
[ 880468-89-3 ]
[ 1253790-58-7 ]
[ 69805-82-9 ]
C₁₆H₂₄N₂O₄ [ No CAS ]
C₁₉H₂₃N₃O₃ [ No CAS ]
C₁₇H₂₆N₂O₄ [ No CAS ]

Reference： [1]Organic Process Research and Development,2019,vol. 23,p. 818 - 824

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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. 86123-95-7 ] {[proInfo.proName]}

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[ 86123-95-7 ] Synthesis Path-Upstream 1~11

[ 86123-95-7 ] Synthesis Path-Downstream 1~31

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Lacosamide Intermediates

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Amino Acid Derivatives

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