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

HRID 268609노트

반응식

HRID 268609 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-0de474de35ce40d2a7c1c8f45353cad4
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446115B2

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