METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE Chemical Properties

Melting point:

157-162°C dec.

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Methanol

form 

Solid

color 

White

optical activity

Consistent with structure

Safety Information

HS Code 

2924297099

METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE Usage And Synthesis

Chemical Properties

White Solid

Uses

Important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins.

Synthesis

General procedure for the synthesis of methyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate hydrochloride from compound (CAS: 75760-11-1): 3-amino-N-[(benzyloxy)carbonyl]-L-alanine methyl ester (5.0 g, 21.0 mmol) and anhydrous methanol (100 mL) were added to a flask fitted with a magnetic stir bar. HCl gas was passed into the solution/slurry for about 10 minutes under stirring conditions. After about 2 minutes, an exothermic reaction was observed and the solution changed from turbid white to clear/colorless. After stirring the reaction solution overnight, it was concentrated and dried by vacuum to afford methyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propionate hydrochloride (6.0 g, 98% yield) as white crystals.1H NMR (δ): 3.05 (t, 1H), 3.19 (t, 1H), 3.70 (s, 3H), 4.45 (m, 1H), 5.10 ( s, 2H), 7.38 (m, 5H), 7.95 (d, 1H), 8.35 (br s, 3H).LCMS (ES, M + H = 253).

References

[1] Patent: WO2006/106326, 2006, A1. Location in patent: Page/Page column 99

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