Acetic Anhydride → 3-Formamido-3-phenylpropanoic acid

HRID 132068

반응식

HRID 132068 반응식
[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]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 69189DL-beta-Phenylalanine

생성물 1

HCID 148266033-Formamido-3-phenylpropanoic acid수율 91%

시약·촉매·용매 1

HCID 284Formic Acid용매2회

반응 조건

온도
50 °C

실험 절차

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.).

후처리

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

출처 및 근거

ORD 기록
ord-32f75bac5fcc4d8c86c772f771f3280b
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07385080B2

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