Potassium Hydroxide → N-((1R)-1-Phenylethyl)glycine

HRID 1842706Notes

Reaction equation

HRID 1842706 reaction equation
[C:1]1([C@H:7]([NH:9][CH2:10][C:11]([O:13]C)=[O:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>>[C:1]1([C@H:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 40493097HCID 40493097, compound2×

Product 1

HCID 28897015N-((1R)-1-Phenylethyl)glycineYield 91.1%

Procedure

Methyl 2-{[(1R)-1-phenylethyl]amino}acetate (Intermediate 44, 587.0 g, 3.0 mol) was refluxed in aqueous KOH (3.36 g, 0.06 mol dissolved in 2.5 L water) overnight. The phases were then separated and the aqueous solution was washed with EtOAc (3×1 L). The combined organic solutions were concentrated in vacuo to give the title compound (490 g, 90%) as white solid; 1H NMR: 1.48 (3H, d), 2.89 (1H, d), 3.00 (1H, d), 4.20 (1H, m), 7.37-7.43 (5H, m).

Workup

  1. customThe phases were then separated
  2. washthe aqueous solution was washed with EtOAc (3×1 L)
  3. concentrationThe combined organic solutions were concentrated in vacuo

Sources & evidence

ORD record
ord-b029e1f2a09247bc86fc1a2ed13b9a37
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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