HCID 86733267, compound → N-Acetyl-DL-phenylglycine

HRID 1606259

Reaction equation

HRID 1606259 reaction equation
[C:1]([NH:4][C:5](C1SC=CC=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1C)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]>[Ni].CC(C)=O>[C:1]([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86733267HCID 86733267, compound

Product 1

HCID 85935N-Acetyl-DL-phenylglycineYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 180AcetoneSolvent

Procedure

Two (2.0) cc of Raney nickel (WII) was suspended in 15 ml of acetone, and refluxed for 7 minutes. Cooling the suspension to room temperature, 315 mg of α-acetylamino-α-tolylthiophenylacetic acid was added, followed by 5.5 hours' stirring at room temperature. The insoluble matter was separated by filtration, and washed with ethanol. The filtrate and washing were combined and concentrated under reduced pressure. The residue was crystallized from an ether-n-hexane system. Thus 141 mg of α-acetylaminophenylacetic acid was obtained. The yield was 73%.

Workup

  1. temperaturerefluxed for 7 minutes
  2. customThe insoluble matter was separated by filtration
  3. washwashed with ethanol
  4. washThe filtrate and washing
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from an ether-n-hexane system

Sources & evidence

ORD record
ord-386f7d6536084da18b1ad9a9baae91ff
Source dataset
uspto-grants-1976_04
Patent number
US03952044

Linked notes

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