L-Serine → Benzyl 2-amino-3-hydroxypropanoate

HRID 1906988Notes

Reaction equation

HRID 1906988 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[Br-].[Li+].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN1CCCC1=O>[NH2:1][CH:2]([CH2:3][OH:4])[C:5]([O:7][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 5951L-SerineHCID 7498Benzyl BromideHCID 82050Lithium Bromide

Product 1

HCID 3788223Benzyl 2-amino-3-hydroxypropanoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a similar manner 1.09 grams (0.0105 mole) of serine, 1.76 grams (0.02 mole) of lithium bromide, 2.02 grams (0.0118 mole) of benzyl bromide and 16 grams of N-methylpyrrolidinone were stirred together at 25° C. for 16 hours and at 50° C. for 3 hours to obtain the desired benzyl α-amino-β-hydroxypropionate product. High pressure liquid chromatographic assay indicated a 86 percent yield of the desired product.

Sources & evidence

ORD record
ord-dd50a23a8f9a43b38ce5a532536d3949
Source dataset
uspto-grants-1987_03
Patent number
US04654433

Reaction notes

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