Sodium Hydroxide → 1-[1-Benzyloxycarbonyl-4-(S)-fluoro-3-(S)-pyrrolidinyl]-cyclopropanecarboxylic acid

HRID 1954613노트

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HRID 1954613 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([C:16]2([C:19]([O:21]CC)=[O:20])[CH2:18][CH2:17]2)[C@H:13]([F:24])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][C@@H:13]([F:24])[C@@H:14]([C:16]2([C:19]([OH:21])=[O:20])[CH2:18][CH2:17]2)[CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 110350361-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidine

생성물 1

HCID 109797271-[1-Benzyloxycarbonyl-4-(S)-fluoro-3-(S)-pyrrolidinyl]-cyclopropanecarboxylic acid수율 92.1%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

1-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonyl-cyclopropyl)-3-(S)-fluoropyrrolidine (4.67 g, 13.92 mmol) was dissolved in ethanol (50 ml), and a 1 N sodium hydroxide aqueous solution (50 ml) was added dropwise to the resulting solution. The reaction solution was stirred at 40° C. for 1.5 hours and then ethanol was evaporated under reduced pressure. The resulting residue was mixed with water (50 ml) and washed with chloroform (100 ml), and the thus separated aqueous layer was acidified by adding dropwise 1 N hydrochloric acid and extracted with chloroform (200 ml×2) and then with diethyl ether (100 ml). The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 3.94 g (92.1%) of the title compound as a colorless amorphous substance.

후처리

  1. customethanol was evaporated under reduced pressure
  2. additionThe resulting residue was mixed with water (50 ml)
  3. washwashed with chloroform (100 ml)
  4. additionby adding dropwise 1 N hydrochloric acid
  5. extractionextracted with chloroform (200 ml×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5329016e773c42289321674a4803ae48
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121285

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