| Identification | Back Directory | [Name]
METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE | [CAS]
35761-27-4 | [Synonyms]
Z-Dap-OMe.HCl
Z-L-Dap-OMe*HCl
Methyl 2-(S)-[N-Carbobenzyloxy]amino-3-aminopropionate
3-Amino-N-[(phenylmethoxy)carbonyl]-L-alanine methyl ester
METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE
3-AMino-N-[(phenylMethoxy)carbonyl]-L-alanine Methyl Ester Hydrochloride
Nα-Z-L-2,3-diaminopropionic acid methyl ester hydrochloride≥ 98.5% (HPLC)
methyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate hydrochloride
METHYL 2-(S)-[N-(BENZYLOXY)CARBONYL]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE | [Molecular Formula]
C12H17ClN2O4 | [MDL Number]
MFCD03701202 | [MOL File]
35761-27-4.mol | [Molecular Weight]
288.73 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
157-162°C dec. | [storage temp. ]
Refrigerator | [solubility ]
Chloroform, Methanol | [form ]
Solid | [color ]
White | [Optical Rotation]
Consistent with structure |
| Hazard Information | Back Directory | [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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