Product Name

  • Name

    D-Serine methyl ester hydrochloride

  • EINECS 611-745-1
  • CAS No. 5874-57-7
  • Article Data40
  • CAS DataBase
  • Density 1.62 g/cm3
  • Solubility
  • Melting Point 163-166 °C(lit.)
  • Formula C4H10ClNO3
  • Boiling Point 234.7 °C at 760 mmHg
  • Molecular Weight 155.581
  • Flash Point 95.8 °C
  • Transport Information
  • Appearance White Solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 5874-57-7 (D-Serine methyl ester hydrochloride)
  • Hazard Symbols IrritantXi
  • Synonyms D-Serine,methyl ester, hydrochloride (9CI);Serine, methyl ester, hydrochloride, D-(8CI);(R)-2-Amino-3-hydroxypropionic acid methyl ester hydrochloride;(R)-Methyl 2-amino-3-hydroxypropanoate hydrochloride;Methyl D-serinatehydrochloride;H-D-Ser-OMe·HCl;
  • PSA 72.55000
  • LogP -0.01870

Synthetic route

methanol
67-56-1

methanol

D-Serine
312-84-5

D-Serine

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

Conditions
ConditionsYield
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
67-56-1

methanol

D-Serine
312-84-5

D-Serine

acetyl chloride
75-36-5

acetyl chloride

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

Conditions
ConditionsYield
Stage #1: methanol; acetyl chloride for 0.0833333h; Cooling with ice;
Stage #2: D-Serine for 2h; Reflux;
97%
D-Serine
312-84-5

D-Serine

acetyl chloride
75-36-5

acetyl chloride

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

Conditions
ConditionsYield
In methanol for 15.5h; Reflux;91%
R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

benzyl chloroformate
501-53-1

benzyl chloroformate

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate
93204-36-5

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

Conditions
ConditionsYield
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 hydrogencarbonate80%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
95715-85-8

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

Conditions
ConditionsYield
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
32315-10-9

bis(trichloromethyl) carbonate

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester
144542-43-8

(R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Heating;100%
In tetrahydrofuran for 4h; Reflux; Inert atmosphere;98%
In tetrahydrofuran at 0 - 80℃; for 2h;75%
trityl chloride
76-83-5

trityl chloride

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(2R)-3-hydroxy-2-(tritylamino)propanoic acid methyl ester
116457-91-1

(2R)-3-hydroxy-2-(tritylamino)propanoic acid methyl ester

Conditions
ConditionsYield
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
5874-57-7

R-(-)-serine methyl ester hydrochloride

benzaldehyde
100-52-7

benzaldehyde

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate
123639-56-5, 131110-76-4, 144001-42-3

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropionic acid methyl ester
874817-14-8

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropionic acid methyl ester

Conditions
ConditionsYield
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%
R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

2,2-Dimethylmalonyl chloride
5659-93-8

2,2-Dimethylmalonyl chloride

N,N'-bis[(1R)-(1-methoxycarbonyl)-2-hydroxyethyl]-2,2-propanedicarboxamide

N,N'-bis[(1R)-(1-methoxycarbonyl)-2-hydroxyethyl]-2,2-propanedicarboxamide

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃; Inert atmosphere;99%
dimethoxyacetaldehyde
51673-84-8

dimethoxyacetaldehyde

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(2R)-2-(2,2-dimethoxyethylamino)-3-hydroxypropionic acid methyl ester

(2R)-2-(2,2-dimethoxyethylamino)-3-hydroxypropionic acid methyl ester

Conditions
ConditionsYield
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,
383-63-1

ethyl trifluoroacetate,

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester
312-84-5

(R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester

Conditions
ConditionsYield
In methanol at 20℃; for 15h;98%
R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

(R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester
312-84-5

(R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 6h;98%
tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tert-butyldiphenylsilyloxy)propanoate
171564-48-0

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tert-butyldiphenylsilyloxy)propanoate

Conditions
ConditionsYield
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
1613522-41-0

1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl 4-methylbenzenesulfonate

R-(-)-serine methyl ester hydrochloride
5874-57-7

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
1613522-64-7

methyl (R)-2-((1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)amino)-3-hydroxypropanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 1h;97%
dehydroabietic acid
1740-19-8

dehydroabietic acid

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

methyl N-(abiet-8,11,13-trien-18-yl)-D-serinate

methyl N-(abiet-8,11,13-trien-18-yl)-D-serinate

Conditions
ConditionsYield
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
201230-82-2

carbon monoxide

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(1R)-2-iodo-1,7,7-trimethylbicyclo<2.2.1>hept-2-ene
22885-95-6

(1R)-2-iodo-1,7,7-trimethylbicyclo<2.2.1>hept-2-ene

C15H23NO4

C15H23NO4

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 1h; diastereoselective reaction;96%
benzyl bromide
100-39-0

benzyl bromide

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(R)-methyl 2-(dibenzylamino)-3-hydroxypropanoate
202478-34-0

(R)-methyl 2-(dibenzylamino)-3-hydroxypropanoate

Conditions
ConditionsYield
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%
Divinyl sulfone
77-77-0

Divinyl sulfone

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

methyl (R)-2-(1,1-dioxidothiomorpholino)-3-hydroxy propanoate

methyl (R)-2-(1,1-dioxidothiomorpholino)-3-hydroxy propanoate

Conditions
ConditionsYield
With ethanol; triethylamine In 1,4-dioxane at 85℃; for 3h;95%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

C18H26N2O6

C18H26N2O6

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃;95%
carbon monoxide
201230-82-2

carbon monoxide

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(1S,4S)-2-iodobornene

(1S,4S)-2-iodobornene

C15H23NO4

C15H23NO4

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 1h; diastereoselective reaction;95%
R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(R)-2-[(1-{4-[(3,5-Dimethyl-phenylcarbamoyl)-methyl]-phenoxy}-cyclopentanecarbonyl)-amino]-3-hydroxy-propionic acid methyl ester
328236-00-6

(R)-2-[(1-{4-[(3,5-Dimethyl-phenylcarbamoyl)-methyl]-phenoxy}-cyclopentanecarbonyl)-amino]-3-hydroxy-propionic acid methyl ester

Conditions
ConditionsYield
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
62910-63-8

5-bromo-2-methoxybenzoyl chloride

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

(R)-2-(5-Bromo-2-methoxy-benzoylamino)-3-hydroxy-propionic acid methyl ester
380223-64-3

(R)-2-(5-Bromo-2-methoxy-benzoylamino)-3-hydroxy-propionic acid methyl ester

Conditions
ConditionsYield
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%
R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

acetyl chloride
75-36-5

acetyl chloride

(R)-methyl 2-acetamido-3-hydroxypropionate

(R)-methyl 2-acetamido-3-hydroxypropionate

Conditions
ConditionsYield
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
4480-47-1

t-butylglyoxal

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

methyl (R)-2-tert-butyloxazolidine-4-carboxylate
257291-68-2

methyl (R)-2-tert-butyloxazolidine-4-carboxylate

Conditions
ConditionsYield
With triethylamine In pentane at 55℃; for 72h; Dean Stark conditions; optical yield given as %de;94%
C25H24N8O8S

C25H24N8O8S

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

C29H31N9O10S

C29H31N9O10S

Conditions
ConditionsYield
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
5874-57-7

R-(-)-serine methyl ester hydrochloride

Fmoc-Thr-OH
73731-37-0

Fmoc-Thr-OH

(R)-2-[(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-hydroxy-propionic acid methyl ester
609359-05-9

(R)-2-[(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-hydroxy-propionic acid methyl ester

Conditions
ConditionsYield
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
5874-57-7

R-(-)-serine methyl ester hydrochloride

benzoyl chloride
98-88-4

benzoyl chloride

N-benzoyl-D-serine methyl ester
1040384-28-8

N-benzoyl-D-serine methyl ester

Conditions
ConditionsYield
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
98204-51-4

(S)-2-[{(allyloxy)carbonyl}amino]-4-methylpentanoic acid

R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

N-(N-(prop-2-enyloxycarbonyl)-L-leucyl)-D-serine methyl ester

N-(N-(prop-2-enyloxycarbonyl)-L-leucyl)-D-serine methyl ester

Conditions
ConditionsYield
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
5874-57-7

R-(-)-serine methyl ester hydrochloride

benzimidic acid ethyl ester
825-60-5

benzimidic acid ethyl ester

(R)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
105308-52-9

(R)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Conditions
ConditionsYield
In 1,2-dichloro-ethane91.4%
In dichloromethane; water for 24h; Ambient temperature;75.3%
In 1,2-dichloro-ethane for 20h; Heating / reflux;
R-(-)-serine methyl ester hydrochloride
5874-57-7

R-(-)-serine methyl ester hydrochloride

2-naphthaloyl chloride
2243-83-6

2-naphthaloyl chloride

N-(2-naphthoyl)-D-serine methyl ester
1312671-66-1

N-(2-naphthoyl)-D-serine methyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h;91%

D-Serine methyl ester hydrochloride Chemical Properties

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

D-Serine methyl ester hydrochloride Safety Profile

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 Specification

  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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