2-Propanethiol → N-Acetyl-DL-phenylglycine

HRID 1606262

Reaction equation

HRID 1606262 reaction equation
[C:1]([NH:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(SC)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].C(S)(C)C.C(=O)([O-])[O-].[K+].[K+].CO.O>O>[C:1]([NH:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 63642-PropanethiolHCID 11430Potassium CarbonateHCID 21485357HCID 21485357, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 85935N-Acetyl-DL-phenylglycineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

340 Milligrams of N-acetylamino-α-methylthiophenylacetic acid, 240 mg of isopropyl mercaptan, and 351 mg of potassium carbonate were added to 10 ml of a methanol-water mixture (9:1), and refluxed for 3 hours. Following a reduced pressure concentration of the reaction mixture to approximately 1 ml, 20 ml of water was added to the concentrate, which was then extracted with ethyl acetate. The organic phase was dried with Glauber's salt, and concentrated under reduced pressure. The residue was crystallized from an ether-n-hexane system, to provide 247 mg of α-acetylaminophenylacetic acid. The yield was 90%.

Workup

  1. temperaturerefluxed for 3 hours
  2. additionwas added to the concentrate, which
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe organic phase was dried with Glauber's salt
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from an ether-n-hexane system

Sources & evidence

ORD record
ord-04b398770649450197f0fe3c0087c7da
Source dataset
uspto-grants-1976_04
Patent number
US03952044

Linked notes

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