| Identification | Back Directory | [Name]
(R)-methyl 2-(dibenzylamino)propanoate | [CAS]
188798-80-3 | [Synonyms]
(R)-methyl 2-(dibenzylamino)propanoate
methyl (R)-2-(N,N-dibenzylamino)propanoate
D-Alanine, N,N-bis(phenylmethyl)-, methyl ester | [Molecular Formula]
C18H21NO2 | [MDL Number]
MFCD31651414 | [MOL File]
188798-80-3.mol | [Molecular Weight]
283.36 |
| Hazard Information | Back Directory | [Synthesis]
Starting with D-alanine, N,N-dibenzyl-D-alanine is generated by reflux reaction with excess benzyl bromide in an alkaline aqueous solution of potassium carbonate and sodium hydroxide (or an ethanol/water mixture) via nucleophilic substitution. Subsequently, the resulting dibenzyl amino acid is reacted with methyl iodide in dimethylformamide (DMF) or esterified in methanol via thionyl chloride (SOCl₂) catalysis to efficiently obtain (R)-methyl 2-(dibenzylamino)propanoate. | [References]
[1] PROF. DR. MANFRED T. REETZ Alfred S Mark W Drewes. Stereoselective Synthesis of β-Amino Alcohols from Optically Active α-Amino Acids†[J]. Angewandte Chemie International Edition, 1987, 26 11: 1141-1143. DOI:10.1002/anie.198711411. |
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Tcichem, Inc.
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