Methanol → 1-[2-(4-Chloro-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea

HRID 430113Notes

Reaction equation

HRID 430113 reaction equation
C(O[C:4](=[O:19])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[CH3:20][NH:21][C:22]([NH2:24])=[O:23].C[O-].[Mg+2].C[O-].CO>>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH:5]([CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[C:4]([NH:24][C:22]([NH:21][CH3:20])=[O:23])=[O:19])=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 462211542-(4-Chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester

Product 1

HCID 120444531-[2-(4-Chloro-phenyl)-3-cyclopentyl-propionyl]-3-methyl-ureaYield 5.8%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester (1.65 g, 5.89 mmol) and methyl urea (654 mg, 8.83 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 16.9 mL, 11.78 mmol) was refluxed at 100° C. for 6 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 1-[2-(4-chloro-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (105.3 mg, 5.8%) as a white solid: mp 145-147° C.; EI-HRMS m/e calcd for C16H21ClN2O2 (M+) 308.1292, found 308.1291. The methyl ester of the starting material was recovered from the reaction mixture due to transesterification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-cf574923e2dc4db0b306c0ff2fcb85ec
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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