Triethylamine → [(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl] acetic acid

HRID 225962

반응식

HRID 225962 반응식
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=O)[CH2:11][C@H:10]2[CH2:15][C:16]([OH:18])=[O:17])=[O:8])=[CH:3][CH:2]=1.[CH3:25][O:26][NH3+:27].[Cl-].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:27][O:26][CH3:25])[CH2:11][C@H:10]2[CH2:15][C:16]([OH:18])=[O:17])=[O:8])=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 69036428[(2s)-1-(Biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetic acid2회

생성물 1

HCID 131727525[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl] acetic acid수율 48.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetic acid (Intermediate 5, 1.50 g, 6.64 mmol), hydroxylamine methyl ether hydrochloride (0.58 g, 6.96 mmol) and triethylamine (1.62 ml, 11.60 mmol) in chloroforme (30 ml) was stirred at RT for 2 days Solvent was removed under reduced pressure and the residue was taken up in ethyl acetate. Organic phase was washed twice with a solution of citric acid 10% and once with brine. Organic phase was then dried on MgSO4, filtered, and concentrated to give [(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid as a cream solid (1.14 g). Yield: 45%. HLPC purity: 92%

후처리

  1. customwas removed under reduced pressure
  2. washOrganic phase was washed twice with a solution of citric acid 10% and once with brine
  3. customOrganic phase was then dried on MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5a0a347e841840a688139dd8ff711e73
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557136B2

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