Methylamine → (S)-2-Hydroxy-N-methyl-2-phenylacetamide

HRID 2358014Notes

Reaction equation

HRID 2358014 reaction equation
[C:1]([O:11]C)(=O)[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH3:13][NH2:14]>CO>[OH:3][C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([NH:14][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 6329Methylamine3×HCID 643570methyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 12281461(S)-2-Hydroxy-N-methyl-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Methyl (S)-(+)-mandelate (17 g) is dissolved in a solution of methylamine in methanol (230 mL, 2.0 M) and kept at RT for 1 d. Another portion of methylamine in methanol (10 mL, 2.0 M) is added. A third portion of methylamine in methanol (10 mL, 2.0 M) is added one day later. After additional 24 h the solvents are removed in vacuo to give the desired mandelamide as pale yellow crystals, which are used without further purification.

Workup

  1. customAfter additional 24 h the solvents are removed in vacuo

Sources & evidence

ORD record
ord-ee307858920a47ca811f5f7b6b342cee
Source dataset
uspto-grants-2010_07
Patent number
US07763638B2

Reaction notes

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