2-Bromo-1-(2-ethylphenyl)ethan-1-one → (S)-2-{[5-(2-Ethyl-benzoyl)-thiazol-2-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 914725

반응식

HRID 914725 반응식
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]([N:17]=[CH:18]N(C)C)=[S:16])=[O:7])([CH3:4])[CH3:3].Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH3:33])=[O:25]>CN(C)C=O.ClCCl>[C:2]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]1[S:16][C:23]([C:24](=[O:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][CH3:33])=[CH:18][N:17]=1)=[O:7])([CH3:1])([CH3:3])[CH3:4]

참가 물질

5

반응물 2

HCID 234426012-Bromo-1-(2-ethylphenyl)ethan-1-oneHCID 865965202-(S)-(3-dimethylaminomethylene-thioureidomethyl)-pyrrolidine-1-carboxylic acid 1,1-dimethylethyl ester

생성물 1

HCID 11407360(S)-2-{[5-(2-Ethyl-benzoyl)-thiazol-2-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester수율 65.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(S)-(3-dimethylaminomethylene-thioureidomethyl)-pyrrolidine-1-carboxylic acid 1,1-dimethylethyl ester (150 mg) in N,N-dimethylformamide (2 ml) was added 2-bromo-1-(2-ethylphenyl)-ethanone (109 mg). The mixture was stirred 65 h at room temperature, diluted with dichloromethane, washed twice with water, once with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (2:1 ethyl acetate/hexane eluant) to afford the product as yellow oil (129 mg, 65%).

후처리

  1. washwashed twice with water, once with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (2:1 ethyl acetate/hexane eluant)

출처 및 근거

ORD 기록
ord-bf3e490fcf9b45348465e83ac676c10c
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265109B2

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