3-(2-hydroxy-cyclopentyl)-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide → 2-(4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide

HRID 854783Notes

Reaction equation

HRID 854783 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH:8]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)[C:9]([NH:11][C:12]1[S:13][CH:14]=[CH:15][N:16]=1)=[O:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:8]([CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[CH:18][CH:19]=1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 100007313-(2-hydroxy-cyclopentyl)-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide2×HCID 178418287HCID 178418287, compound2×

Product 1

HCID 103404942-(4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamideYield 14.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-(2-hydroxy-cyclopentyl)-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide (prepared as in Example 26, 72.4 mg, 0.184 mmol) in methylene chloride (1.8 mL) was treated with pyridinium chlorochromate (20 wt. % on basic alumina, 237.3 mg, 0.22 mmol). The resulting reaction mixture was stirred at 25° C. for 3 h, at which time, thin layer chromatography indicated a small amount of the 3-(2-hydroxy-cyclopentyl)-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide. The reaction mixture was then treated with an additional amount of pyridinium chlorochromate (20 wt. % on basic alumina, 237.3 mg, 0.220 mmol). The reaction mixture was allowed to stir at 25° C. for 4 h and then filtered through a pad of celite. The pad of celite was washed well with ethyl acetate until the washings indicated the absence of product by thin layer chromatography. The filtrate was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/7 hexanes/ethyl acetate) afforded 2-(4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide (10.2 mg, 14%) as a white solid: mp 228-230° C.; EI-HRMS m/e calcd for C18H20N2O4S2 (M+) 392.0865. found 392.0871.

Workup

  1. customThe resulting reaction mixture
  2. stirringto stir at 25° C. for 4 h
  3. filtrationfiltered through a pad of celite
  4. washThe pad of celite was washed well with ethyl acetate until the washings
  5. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-31d15ec5a54b4008be3950a04f26f589
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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