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

HRID 635106노트

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HRID 635106 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-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidine (4.67 g, 13.92 mmol) was dissolved in ethanol (50 ml). Then a 1 N aqueous solution of sodium hydroxide (50 ml) was added dropwise into this solution. Then the liquid reaction mixture was stirred at 40° C. for 1.5 hours and ethanol was removed by evaporation under reduced pressure. Water (50 ml) was added to the residue followed by washing with chloroform (100 ml). The aqueous layer was separated and acidified by adding dropwise 1 N hydrochloric acid thereinto. Next, it was extracted successively with chloroform (200 ml×2) and diethyl ether (100 ml). The combined organic layer was dried over anhydrous sodium sulfate. After filtering, 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. customThen the liquid reaction mixture
  2. customethanol was removed by evaporation under reduced pressure
  3. additionWater (50 ml) was added to the residue
  4. washby washing with chloroform (100 ml)
  5. customThe aqueous layer was separated
  6. additionby adding dropwise 1 N hydrochloric acid
  7. extractionNext, it was extracted successively with chloroform (200 ml×2) and diethyl ether (100 ml)
  8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  9. filtrationAfter filtering
  10. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2d3e4e38e191486f9072865c01225d4e
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184388B2

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