Conditions | Yield |
---|---|
With acetyl chloride for 2.5h; Heating; | 100% |
Stage #1: methanol; D-Serine With acetyl chloride at 0℃; Stage #2: In methanol for 3h; Heating; | 100% |
With hydrogenchloride In water at 55℃; | 100% |
methanol
D-Serine
acetyl chloride
R-(-)-serine methyl ester hydrochloride
Conditions | Yield |
---|---|
Stage #1: methanol; acetyl chloride for 0.0833333h; Cooling with ice; Stage #2: D-Serine for 2h; Reflux; | 97% |
Conditions | Yield |
---|---|
In methanol for 15.5h; Reflux; | 91% |
R-(-)-serine methyl ester hydrochloride
benzyl chloroformate
(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; Cooling with ice; | 100% |
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 12h; | 91% |
With sodium hydrogencarbonate | 80% |
di-tert-butyl dicarbonate
R-(-)-serine methyl ester hydrochloride
2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: R-(-)-serine methyl ester hydrochloride With triethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 16.5h; Cooling with ice; | 100% |
With triethylamine In tetrahydrofuran at 0 - 140℃; for 0.333333h; Inert atmosphere; Microwave irradiation; | 99% |
With triethylamine In tetrahydrofuran at 0 - 50℃; for 17h; Inert atmosphere; | 97% |
bis(trichloromethyl) carbonate
R-(-)-serine methyl ester hydrochloride
(R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran for 4h; Heating; | 100% |
In tetrahydrofuran for 4h; Reflux; Inert atmosphere; | 98% |
In tetrahydrofuran at 0 - 80℃; for 2h; | 75% |
trityl chloride
R-(-)-serine methyl ester hydrochloride
(2R)-3-hydroxy-2-(tritylamino)propanoic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In chloroform at 0℃; for 1h; | 99% |
With triethylamine In 1,2-dichloro-ethane at 50℃; for 12h; | 97% |
With triethylamine In dichloromethane at 0 - 25℃; for 16h; | 95% |
R-(-)-serine methyl ester hydrochloride
benzaldehyde
methyl (2R)-2-(benzylamino)-3-hydroxypropanoate
Conditions | Yield |
---|---|
Stage #1: R-(-)-serine methyl ester hydrochloride; benzaldehyde With magnesium sulfate; triethylamine In dichloromethane at 20℃; for 24h; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 3h; Further stages.; | 99% |
Stage #1: R-(-)-serine methyl ester hydrochloride With triethylamine In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: benzaldehyde In methanol at 20℃; for 2h; Inert atmosphere; Stage #3: With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere; | 99% |
Stage #1: R-(-)-serine methyl ester hydrochloride; benzaldehyde With triethylamine Stage #2: With sodium tetrahydroborate | 79% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
R-(-)-serine methyl ester hydrochloride
2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropionic acid methyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane; water cooling; | 99% |
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 4.33333h; | 95% |
Conditions | Yield |
---|---|
With triethylamine In chloroform at 0 - 20℃; Inert atmosphere; | 99% |
dimethoxyacetaldehyde
R-(-)-serine methyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogen; triethylamine; palladium on activated charcoal In methanol; water at 20℃; for 16h; | 98% |
With palladium 10% on activated carbon; hydrogen; triethylamine In methanol; water at 20℃; |
ethyl trifluoroacetate,
R-(-)-serine methyl ester hydrochloride
(R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester
Conditions | Yield |
---|---|
In methanol at 20℃; for 15h; | 98% |
R-(-)-serine methyl ester hydrochloride
trifluoroacetic anhydride
(R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 6h; | 98% |
tert-butyldicarbonate
R-(-)-serine methyl ester hydrochloride
tert-butylchlorodiphenylsilane
methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tert-butyldiphenylsilyloxy)propanoate
Conditions | Yield |
---|---|
Stage #1: tert-butyldicarbonate; R-(-)-serine methyl ester hydrochloride With sodium hydrogencarbonate In tetrahydrofuran; water Stage #2: tert-butylchlorodiphenylsilane With 1H-imidazole In dichloromethane | 98% |
1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl 4-methylbenzenesulfonate
R-(-)-serine methyl ester hydrochloride
methyl (R)-2-((1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)amino)-3-hydroxypropanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 1h; | 97% |
Conditions | Yield |
---|---|
Stage #1: dehydroabietic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: R-(-)-serine methyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 1h; | 97% |
carbon monoxide
R-(-)-serine methyl ester hydrochloride
(1R)-2-iodo-1,7,7-trimethylbicyclo<2.2.1>hept-2-ene
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 1h; diastereoselective reaction; | 96% |
benzyl bromide
R-(-)-serine methyl ester hydrochloride
(R)-methyl 2-(dibenzylamino)-3-hydroxypropanoate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 24h; Alkylation; | 95% |
With sodium hydrogencarbonate; sodium iodide In tetrahydrofuran; dimethyl sulfoxide for 2h; Heating; | 92% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 5h; | 91.7% |
Conditions | Yield |
---|---|
With ethanol; triethylamine In 1,4-dioxane at 85℃; for 3h; | 95% |
N-tert-butoxycarbonyl-L-phenylalanine
R-(-)-serine methyl ester hydrochloride
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; | 95% |
carbon monoxide
R-(-)-serine methyl ester hydrochloride
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 1h; diastereoselective reaction; | 95% |
R-(-)-serine methyl ester hydrochloride
JP-7
(R)-2-[(1-{4-[(3,5-Dimethyl-phenylcarbamoyl)-methyl]-phenoxy}-cyclopentanecarbonyl)-amino]-3-hydroxy-propionic acid methyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; | 94.7% |
5-bromo-2-methoxybenzoyl chloride
R-(-)-serine methyl ester hydrochloride
(R)-2-(5-Bromo-2-methoxy-benzoylamino)-3-hydroxy-propionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: R-(-)-serine methyl ester hydrochloride With triethylamine In chloroform at -5℃; for 0.0833333h; Stage #2: 5-bromo-2-methoxybenzoyl chloride With triethylamine In chloroform at 0 - 20℃; for 0.25h; | 94% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; | 94% |
With triethylamine In dichloromethane at -10 - 5℃; for 3h; | 90% |
With triethylamine In dichloromethane at -10 - 0℃; for 3h; Green chemistry; | 90% |
t-butylglyoxal
R-(-)-serine methyl ester hydrochloride
methyl (R)-2-tert-butyloxazolidine-4-carboxylate
Conditions | Yield |
---|---|
With triethylamine In pentane at 55℃; for 72h; Dean Stark conditions; optical yield given as %de; | 94% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1h; | 94% |
R-(-)-serine methyl ester hydrochloride
Fmoc-Thr-OH
(R)-2-[(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-hydroxy-propionic acid methyl ester
Conditions | Yield |
---|---|
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 25℃; for 3h; | 93% |
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃; for 2h; | 70% |
R-(-)-serine methyl ester hydrochloride
benzoyl chloride
N-benzoyl-D-serine methyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 92% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h; | 92% |
With triethylamine In methanol at 0℃; |
(S)-2-[{(allyloxy)carbonyl}amino]-4-methylpentanoic acid
R-(-)-serine methyl ester hydrochloride
Conditions | Yield |
---|---|
Stage #1: (S)-2-[{(allyloxy)carbonyl}amino]-4-methylpentanoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h; Stage #2: R-(-)-serine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 48h; | 92% |
R-(-)-serine methyl ester hydrochloride
benzimidic acid ethyl ester
(R)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane | 91.4% |
In dichloromethane; water for 24h; Ambient temperature; | 75.3% |
In 1,2-dichloro-ethane for 20h; Heating / reflux; |
R-(-)-serine methyl ester hydrochloride
2-naphthaloyl chloride
N-(2-naphthoyl)-D-serine methyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h; | 91% |
Molecular Structure of D-Serine methyl ester hydrochloride (CAS NO.5874-57-7):
The Molecular formula of D-Serine methyl ester hydrochloride (CAS NO.5874-57-7): C4H10ClNO3
The Molecular Weight of D-Serine methyl ester hydrochloride (CAS NO.5874-57-7): 155.58
IUPAC Name: (E)-2-cyano-3-(1-phenyl-3-thiophen-2-ylpyrazol-4-yl)prop-2-enamide
H bond acceptors: 4
H bond donors: 3
Freely Rotating Bonds: 5
Polar Surface Area: 38.77Å2
Melting point: 163-166 °C(lit.)
Boiling Point: 234.7 °C at 760 mmHg
Flash Point: 95.8 °C
Enthalpy of Vaporization: 54.8 kJ/mol
Vapour Pressure: 0.00953 mmHg at 25°C
Appearance: White Solid
Storage temp: -15°C
Product Categories: Amino Acids series; Amino Acids; Amino Acids and Derivatives; All Aliphatics; Amino hydrochloride; Aliphatics; Amino Acids & Derivatives; Amino Acid Derivatives; Peptide Synthesis; Serine
The Hazard Codes of D-Serine methyl ester hydrochloride (CAS NO.5874-57-7): Xi
The Risk Statements information of D-Serine methyl ester hydrochloride (CAS NO.5874-57-7):
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of D-Serine methyl ester hydrochloride (CAS NO.5874-57-7):
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3
D-Serine methyl ester hydrochloride , with CAS number of 5874-57-7, can be called (R)-2-Amino-3-hydroxypropionic acid methyl ester hydrochloride ; (R)-Methyl 2-amino-3-hydroxypropanoate hydrochloride ; Methyl D-serinatehydrochloride ; DL-Serine, methyl ester, hydrochloride ; L-Serine, methyl ester, hydrochloride ; L-serine, methyl ester, hydrochloride (1:1) ; Methyl L-serinate hydrochloride (1:1) . It is a white solid.
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