Acetic Anhydride → 3-(Formylamino)-3-phenylpropanoic acid

HRID 132068ノート

反応式

HRID 132068 の反応式
[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]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 69189DL-beta-Phenylalanine

生成物 1

HCID 148266033-(Formylamino)-3-phenylpropanoic acid収率 91%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒2 回

反応条件

温度
50 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-32f75bac5fcc4d8c86c772f771f3280b
出典データセット
uspto-grants-2008_06
特許番号
US07385080B2

反応ノート

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