D-Serine methyl ester hydrochloride Chemical Properties

Melting point:

163-166 °C(lit.)

alpha 

-4 º (c=4 in ethanol)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in ethanol and methanol.

form 

Liquid

color 

Clear colorless to yellow

optical activity

[α]20/D 4°, c = 4 in ethanol

InChI

InChI=1/C4H9NO3.ClH/c1-8-4(7)3(5)2-6;/h3,6H,2,5H2,1H3;1H/t3-;/s3

InChIKey

NDBQJIBNNUJNHA-AENDTGMFSA-N

SMILES

[C@@H](N)(CO)C(=O)OC.Cl |&1:0,r|

CAS DataBase Reference

5874-57-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29225000

MSDS

• Language:English Provider:SigmaAldrich

D-Serine methyl ester hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

D-Serine Methyl Ester Hydrochloride (cas# 5874-57-7) is a compound useful in organic synthesis.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of D-serine methyl ester hydrochloride from methanol and D-serine: 4.2.1.1 Synthesis of methyl (R)-2-isopropyl-4,5-dihydrooxazole-4-carboxylate First, sulfoxide chloride (SOCl?, 7.60 mL, 104.2 mmol) was slowly added dropwise to a methanolic solution of D-serine (10.0 g, 95.1 mmol) and the reaction mixture was stirred for 24 h at room temperature. After completion of the reaction, the solvent was removed by rotary evaporator to give a white solid. The solid was washed with hexane (3 x 25 mL) to give D-serine methyl ester hydrochloride (14.4 g, 97% yield) as a colorless solid. The product was characterized by 1H NMR (300 MHz, D?O) with the following chemical shifts: δ 4.32-4.28 (1H, m, CH), 4.12 (1H, dd, J = 4.2, 12.5 Hz, CHaHbOH), 4.02 (1H, dd, J = 3.4, 12.5 Hz, CHaHbOH), 3.88 (3H, s, CH?) .

References

[1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 372 - 376
[2] Heterocyclic Communications, 2005, vol. 11, # 3-4, p. 343 - 346
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5716 - 5726
[4] Chemical Communications, 2016, vol. 52, # 55, p. 8612 - 8614
[5] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10162 - 10165

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