D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE Chemical Properties

Melting point:

114-119℃

storage temp. 

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

solubility 

Methanol (Slightly), Water (Slightly)

form 

Solid

color 

Off-White

optical activity

Consistent with structure

InChI

InChI=1/C6H11NO4.ClH/c1-10-5(8)3-4(7)6(9)11-2;/h4H,3,7H2,1-2H3;1H/t4-;/s3

InChIKey

PNLXWGDXZOYUKB-NDILARRWNA-N

SMILES

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

CAS DataBase Reference

69630-50-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

D-Aspartic Acid Dimethyl Ester Hydrochloride is a useful synthetic intermediate in the synthesis of MK-7246 (M425045); a potent and selective CRTH2 antagonist for the treatment of respiratory diseases.

Synthesis

106.8 g (0.8 mol) of D-aspartic acid and 700 ml of methanol were added to the reaction vessel and 84.4 ml (1.2 mol) of thionyl chloride was added slowly dropwise under stirring, controlling the reaction temperature to 0°C. After the dropwise addition, the reaction system was warmed up to room temperature (about 29°C) and the reaction was continued with stirring for 30 hours. Upon completion of the reaction, excess methanol and thionyl chloride were removed from the reaction solution by distillation. The remaining oily material was dissolved in 3.5 times the volume of ether for crystallization to obtain white crystals. After filtration, the crystals were washed with ether three times and dried to finally obtain 107.8 g of white solid DL-aspartic acid dimethyl ester hydrochloride.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10460 - 10474
[2] Journal of Organic Chemistry, 2012, vol. 77, # 5, p. 2299 - 2309
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2936 - 2947
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7215 - 7226
[5] Patent: WO2010/31184, 2010, A1. Location in patent: Page/Page column 22

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