3-(Trifluoromethyl)phenyl isocyanate → N-(1-Benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-2-(S)-[3-(3-trifluoromethyl-phenyl)-ureido]-butyramide

HRID 1242707ノート

反応式

HRID 1242707 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:14][C@@H:15]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20]1)=[O:17]>ClCCl>[CH2:24]([N:21]1[CH2:22][CH2:23][C@@H:19]([NH:18][C:16](=[O:17])[C@@H:15]([NH:14][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=2)=[O:11])[C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:20]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

4

反応物 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 210623362-(S)-Amino-N-(1-benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-butyramide

生成物 1

HCID 10162603N-(1-Benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-2-(S)-[3-(3-trifluoromethyl-phenyl)-ureido]-butyramide収率 34%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(Trifluoromethyl)phenyl isocyanate (0.093 g, 0.50 mmole) was slowly added to a solution of 2a (0.12 g, 0.42 mmole) in dichloromethane (20 mL) at 0° C. The solution was allowed to warm to room temperature and stirred for 18 h. The reaction was then quenched with water (20 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The organic residue was purified by flash chromatographey on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 3a (0.045 g, 34%) as a white solid; MS (EI)=476 (M+).

後処理

  1. customThe reaction was then quenched with water (20 mL)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe organic residue was purified by flash chromatographey on silica gel
  6. washeluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4)

出典と根拠

ORDレコード
ord-9c89d82eb3e449d69e43a2c578a9b3e5
出典データセット
uspto-grants-2006_10
特許番号
US07115664B2

反応ノート

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