Sodium Hydroxide → 4-(S)-(1-Carboxycyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone

HRID 635111ノート

反応式

HRID 635111 の反応式
C([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[O:22])[C@H:10]2[F:23])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])[C:11](=[O:22])[C@H:10]2[F:23])[CH2:7][CH2:8]1)([OH:5])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 109692184-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone

生成物 1

HCID 539799064-(S)-(1-Carboxycyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone収率 89.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone (12.56 g, 39.33 mmol) was dissolved in ethanol (120 ml) and a 1 N aqueous solution of sodium hydroxide (120 ml) was added dropwise thereinto. After stirring at 40° C. for 6 hours, ethanol was evaporated under reduced pressure. The residue was washed with chloroform (100 ml×2). Under ice cooling, the separated aqueous layer was acidified by adding dropwise 1 N hydrochloric acid thereinto and then extracted successively with chloroform (300 ml×2) and diethyl ether (300 ml). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 10.24 g (89.4%) of the title compound as colorless needles.

後処理

  1. customethanol was evaporated under reduced pressure
  2. washThe residue was washed with chloroform (100 ml×2)
  3. additionby adding dropwise 1 N hydrochloric acid
  4. extractionextracted successively with chloroform (300 ml×2) and diethyl ether (300 ml)
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d21024be60c54b59909f8134478ed43e
出典データセット
uspto-grants-2001_02
特許番号
US06184388B2

反応ノート

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