Acetic Anhydride → 3-Formamido-3-phenylpropanoic acid

HRID 132068

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.[NH2:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=[O:12]>C(O)=O>[CH:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=[O:12])=[O:3]

Participants

Conditions

Temperature: 50 °C

Procedure

Formic acid (1.0 ml, 26.6 mmol) was added dropwise to 2.0 ml (21.4 mmol) of acetic anhydride in an ice bath. After that, the ice bath was removed, and the solution was stirred at 50° C. for 15 minutes. After allowing to stand for 15 minutes, the resulting solution was cooled again with an ice bath and was added dropwise to a solution of 586 mg (3.55 mmol) of (±)-3-amino-3-phenylpropanoic acid in 0.5 ml of formic acid previously cooled to a temperature not higher than 10° C. The mixture was stirred for 40 minutes as it was, and, when the solution became room temperature, it was stirred for 80 minutes more. The residue prepared by concentrating the reaction solution in vacuo was recrystallized from water to give 624 mg (3.23 mmol) of (±)-3-formylamino-3-phenylpropanoic acid in a yield of 91.0% (melting point: 127 to 128° C.).

Workup

customAfter that, the ice bath was removed
waitto stand for 15 minutes
temperaturethe resulting solution was cooled again with an ice bath
temperaturepreviously cooled to a temperature not higher than 10° C
stirringThe mixture was stirred for 40 minutes as it
custombecame room temperature
stirringit was stirred for 80 minutes more
customThe residue prepared
concentrationby concentrating the reaction solution in vacuo
customwas recrystallized from water

Sources & evidence

ORD record: ord-32f75bac5fcc4d8c86c772f771f3280b
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07385080B2

Linked notes

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