HCID 10091453, compound → 2-(3,4-dichloro-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide

HRID 2214071Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-N-thiazol-2-yl-propionamide (prepared as in Example 25, 162.5 mg, 0.42 mmol) in methylene chloride (4.2 mL) was treated with pyridinium chlorochromate (20 wt. % on basic alumina, 545 mg, 0.50 mmol). The reaction mixture was stirred at 25° C. for 2 h. At this time, the reaction was filtered through a plug of celite (ethyl acetate as eluent). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide (64.8 mg, 40.1%) as a light tan solid: mp 79–81° C.; EI-HRMS m/e calcd for C17H16Cl2N2O2S (M+H)+ 383.0383, found 383.0384.

Workup

filtrationAt this time, the reaction was filtered through a plug of celite (ethyl acetate as eluent)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-659e94822ace4579aaf303ab3bcf21df
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105671B2

Reaction notes

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