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

Reaction equation

HRID 914725 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-bf3e490fcf9b45348465e83ac676c10c
Source dataset
uspto-grants-2007_09
Patent number
US07265109B2

Linked notes

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