N-Cbz-D-Alanine synthesis
- Product Name:N-Cbz-D-Alanine
- CAS Number:26607-51-2
- Molecular formula:C11H13NO4
- Molecular Weight:223.23
Yield:26607-51-2 89%
Reaction Conditions:
Stage #1:D-Alanine;benzyl chloroformate with sodium hydroxide in water at 0 - 20;
Stage #2: with hydrogenchloride in water; pH=4 - 5
Steps:
II.29.1
II. Indole Preparations; Intermediate 29: Synthesis of tert-Butyl (2R)-2-Methyl-4-(1H-pyrrolo[3,2-b]pyridin-3-yl)piperazine-1-carboxylate; 1. Synthesis of (2R)-2-{[(benzyloxy)carbonyl]amino}propanoic acid; Benzyl chloroformate (168 mmol) is added dropwise to a solution of (2R)-2-(amino)propanoic acid (169 mmol) in 2 M sodium hydroxide (96 mL) at 0° C. and the reaction mixture is maintained for 3 h at rt. The resulting solution is extracted with diethyl ether (50 mL) and the pH of the aqueous layer is adjusted to 4-5 by the addition of 2 N hydrochloric acid. The aqueous layer is extracted two times with ethyl acetate (2×100 mL) and the combined organic layers are dried (sodium sulfate) and concentrated to provide (2R)-2-{[(benzyloxy)carbonyl]amino}propanoic acid in 89% yield as a white solid.
References:
Memory Pharmaceuticals Corporation US2010/16297, 2010, A1 Location in patent:Page/Page column 35-36
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