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

HRID 966560Notes

Reaction equation

HRID 966560 reaction equation
C(O[C:4](=[O:19])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[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:14]1[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][CH:15]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 462211532-(3-Chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester

Product 1

HCID 120444511-[2-(3-Chloro-phenyl)-3-cyclopentyl-propionyl]-3-methyl-ureaYield 8%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(3-chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester (1.70 g, 6.05 mmol) and methyl urea (673 mg, 9.08 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 17.3 mL, 12.1 mmol) was heated under reflux 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-(3-chloro-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (149.1 mg, 8%) as a white solid: mp 52-55° C.; EI-HRMS m/e calcd for C16H21ClN2O2 (M+) 308.1292, found 308.1287. The methyl ester of the starting material was recovered from the reaction mixture due to transesterification.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-22934da936a14e66a1b8e880afc4b8c1
Source dataset
uspto-grants-2005_10
Patent number
US06951945B2

Reaction notes

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