L-Alanine → benzyl (2S)-2-aminopropanoate

HRID 1906989Notes

Reaction equation

HRID 1906989 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[Br-].[Li+].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN1CCCC1=O>[NH2:1][C@H:2]([C:4]([O:6][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 7498Benzyl BromideHCID 82050Lithium Bromide

Product 1

HCID 726858benzyl (2S)-2-aminopropanoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a similar operation, 0.45 gram (0.005 mole) of alanine, 0.87 gram (0.01 mole) of lithium bromide, 0.95 gram (0.0055 mole) of benzyl bromide and 4.8 grams of N-methylpyrrolidinone were stirred together for 5.5 hours at 55° C. to obtain the desired benzyl alaninate product. High pressure liquid chromatographic assay showed yield of the product to be 89 percent.

Sources & evidence

ORD record
ord-cfc221d72d9d44a29cddca406400fd4b
Source dataset
uspto-grants-1987_03
Patent number
US04654433

Reaction notes

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