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

HRID 225962

反応式

HRID 225962 の反応式
[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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 69036428[(2s)-1-(Biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetic acid2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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%

後処理

  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

出典と根拠

ORDレコード
ord-5a0a347e841840a688139dd8ff711e73
出典データセット
uspto-grants-2009_07
特許番号
US07557136B2

関連ノート

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