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

HRID 660019Notes

Reaction equation

HRID 660019 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 3

HCID 887MethanolHCID 6329MethylamineHCID 643570methyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 12281461(S)-2-Hydroxy-N-methyl-2-phenylacetamideYield 95%

Procedure

Methyl (S)-(+)-mandelate 36 (4.60 g, 27.7 mmol, 1.0 eq) was added to a 2M solution of methylamine in methanol, (70 mL, 140 mmol, 5.05 eq) and the mixture was stirred at rt for 24 h. The mixture was concentrated under reduced pressure to a semi-solid. Residual methanol was co-evaporated with toluene (2×50 mL) followed by 1:1 toluene/heptanes (50 mL) to give a white crystalline solid. The solid was triturated with heptanes (50 mL), filtered and dried to give 4.35 g (95%) of 37 as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure to a semi-solid
  2. customto give a white crystalline solid
  3. customThe solid was triturated with heptanes (50 mL)
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-d474be8cc48f4b9fbc2c2d8870bbd503
Source dataset
uspto-grants-2011_12
Patent number
US08084464B2

Reaction notes

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