Water → tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate

HRID 43846ノート

反応式

HRID 43846 の反応式
C(N(CC)CC)C.[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@@H:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][C@H:20]2[OH:32])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15].O>CS(C)=O.ClCCl>[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][C:20]2=[O:32])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]

参加物

6

反応物 3

HCID 962WaterHCID 8471TriethylamineHCID 86648545tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate

生成物 1

HCID 68406285tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate収率 120.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (374 μL, 2.68 mmol) and sulfur trioxide-pyridine complex (256 mg, 1.61 mmol) were added to a mixed solution of tert-butyl trans(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate synthesized in Example (201b) (100 mg, 0.268 mmol) in dimethyl sulfoxide (1 mL) and dichloromethane (1 mL) at room temperature, and the mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain 120 mg of the title compound as an orange foamy substance, which was used for the next reaction without purification.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-776f04e516aa4eaeaf533d0bcbc52b92
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

反応ノート

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