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

反応式

HRID 394025 の反応式
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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 82707Tetrabutylammonium Acetate触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8ce7075e514b496193cfb7e61b49b8a1
出典データセット
uspto-grants-2004_10
特許番号
US06809108B1

関連ノート

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