HCID 53991841、化合物 → (R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 1636164ノート

反応式

HRID 1636164 の反応式
C([O:8][C:9]([C@H:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][N:12]1[C:18](=[O:46])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([N:29]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][C@@H:30]2[C:36]([O:38]CC2C=CC=CC=2)=[O:37])=[O:28])=[CH:22][CH:21]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([C@H:11]1[CH2:15][C:14]([F:16])([F:17])[CH2:13][N:12]1[C:18](=[O:46])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]([N:29]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][C@@H:30]2[C:36]([OH:38])=[O:37])=[O:28])=[CH:24][CH:25]=1)([OH:10])=[O:8]

参加物

4

反応物 1

HCID 53991841HCID 53991841、化合物

生成物 1

HCID 54227571(R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid収率 61%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

0.64 g (0.001 mol) (R)-1-[[4-[2-[(R)-2-Benzyloxycarbonyl-4,4-difluoropyrrolidin-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxlic acid benzyl ester in 20 ml ethanol were hydrogenated at room temperature and atmospheric pressure in the presence of 0.13 g 5% palladium/carbon. After completion of the reaction the catalyst was filtered off, the solvent was distilled off, and the residue was dissolved in dichloromethane. Evaporation gave 0.28 g (61%) (R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid as a light yellow foam. ISP-MS: 478 (MNH4)+; [α]D=+50.3° (c=0.33% in dimethylsulfoxide).

後処理

  1. customwere hydrogenated at room temperature
  2. customAfter completion of the reaction the catalyst
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved in dichloromethane
  6. customEvaporation

出典と根拠

ORDレコード
ord-0717760def544b13bc99b39af78697c2
出典データセット
uspto-grants-2003_01
特許番号
US06512001B1

反応ノート

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