1-[2-(3,4-Dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionyl]-3-methyl-urea → 1-[2-(3,4-Dichloro-phenyl)-3-(3-oxo-cyclopentyl)-propionyl]-3-methyl-urea

HRID 854807Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:17][CH:18]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19]2)[C:10]([NH:12][C:13]([NH:15][CH3:16])=[O:14])=[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]([CH2:17][CH:18]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]2)[C:10]([NH:12][C:13]([NH:15][CH3:16])=[O:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-[2-(3,4-dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionyl]-3-methyl-urea (prepared as in Example 35, 60.5 mg, 0.17 mmol) in methylene chloride (1.68 mL) was treated with pyridinium chlorochromate (20 wt. % on basic alumina, 218 mg, 0.20 mmol). The reaction mixture was stirred at 25° C. for 4 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, 90/10 methylene chloride/methanol) afforded 1-[2-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-propionyl]-3-methyl-urea (45.8 mg, 76.1%) as a white solid: mp 70-74° C.; FAB-HRMS m/e calcd for C16H18Cl2N2O3 (M+H)+ 357.0773. found 357.0768.

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-ca369c631a724274a4c47243cdf8dc58
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259166B2

Reaction notes

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