D-ASPARTIC ACID-BETA-METHYL ESTER Chemical Properties

Melting point:

188-190 °C

Boiling point:

301.7±37.0 °C(Predicted)

Density 

1.299

storage temp. 

Sealed in dry,Room Temperature

pka

2.16±0.23(Predicted)

Appearance

White to off-white Solid

optical activity

23.2°(C=1.00g/100ml MEOH)

D-ASPARTIC ACID-BETA-METHYL ESTER Usage And Synthesis

Definition

ChEBI: Methyl gamma-D-aspartate is a dicarboxylic acid monoester obtained by condensation of the side-chain carboxy group of D-aspartic acid with methanol. It has a role as a bacterial metabolite. It is a D-aspartic acid derivative and a dicarboxylic acid monoester.

Synthesis

At 0 °C, 73.7 mL of acetyl chloride (1.4 eq.) was slowly added dropwise to 250 mL of methanol. Maintaining 0 °C, the mixture was added dropwise to a 250 mL methanol suspension containing 100 g (751 mmol) of (R)-2-aminosuccinic acid. The reaction mixture was stirred at 0 °C for 3 h before gradually warming to room temperature and continuing to stir overnight. Five identical reaction vials were set up in parallel for the same operation. The mixtures from all six reaction flasks were combined and concentrated under reduced pressure. The concentrated residue was treated with methyl tert-butyl ether (MTBE) and the resulting precipitate was filtered and dried under reduced pressure to give (R)-2-amino-4-methoxy-4-oxobutanoic acid (600 g, 90% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, deuterium oxide): δ 4.33 (t, J = 5.5 Hz, 1H), 3.81 (s, 1H), 3.72 (s, 3H), 3.10 (d, J = 4.9 Hz, 2H).

References

[1] Patent: WO2017/89458, 2017, A1. Location in patent: Page/Page column 72
[2] Gazzetta Chimica Italiana, 1986, vol. 116, # 10, p. 607 - 608
[3] Patent: CN106518701, 2017, A. Location in patent: Paragraph 0021-0022

D-ASPARTIC ACID-BETA-METHYL ESTER(21394-81-0)Related Product Information

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• Z-D-ASP(OTBU)-OH H2O
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