Dimethylformamide → (2r)-1-{(2s,4s)-4-Acetoxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-n-{((3r)-1-cyclohexylmethyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide

HRID 394025

반응식

HRID 394025 반응식
C1(CN2CCC[C@H](CNC(C[C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([C@@H:26]3[CH2:30][C@@H:29]([O:31]S(C)(=O)=O)[CH2:28][N:27]3[C:36](=[O:57])[CH2:37][C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:25])=O)C2)CCCCC1.[CH3:58][N:59]([CH3:62])[CH:60]=O>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[C:29]([O:31][C@@H:29]1[CH2:28][N:27]([C:36](=[O:57])[CH2:37][C:38]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:26]([C:24]([N:20]2[CH2:21][CH2:22][CH2:23][C@@H:19]2[C:24]([NH:20][CH2:19][C@H:23]2[CH2:22][CH2:21][CH2:60][N:59]([CH2:62][CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]3)[CH2:58]2)=[O:25])=[O:25])[CH2:30]1)(=[O:31])[CH3:28]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 131724629(2R)-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}-1-{(2S,4R)-4-(methylsulfonyloxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxyamide

생성물 1

HCID 12149972(2r)-1-{(2s,4s)-4-Acetoxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-n-{((3r)-1-cyclohexylmethyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide

시약·촉매·용매 2

HCID 82707Tetrabutylammonium Acetate촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 40 mg of (2R)-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}-1-{(2S,4R)-4-(methylsulfonyloxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxyamide and 30 mg of tetrabutylammonium acetate in 1 ml of N,N-dimethylformamide was stirred at 85° C. for 15 hours under heating. The reaction liquid was diluted with ethyl acetate, successively washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art. 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/8/1), to provide 14 mg of the title compound as a colorless oily substance.

후처리

  1. temperatureunder heating
  2. customThe reaction liquid
  3. washsuccessively washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art. 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/8/1)

출처 및 근거

ORD 기록
ord-8ce7075e514b496193cfb7e61b49b8a1
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809108B1

연결된 노트

불러오는 중…