Methanol → 1-(2-Biphenyl-4-yl-3-cyclopentyl-propionyl)-3-methyl urea

HRID 1935270Notes

Reaction equation

HRID 1935270 reaction equation
CO[C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:24][NH:25][C:26]([NH2:28])=[O:27].C[O-].[Mg+2].C[O-].CO>>[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:16][C:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([NH:28][C:26]([NH:25][CH3:24])=[O:27])=[O:23])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 674835462-Biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester

Product 1

HCID 99030271-(2-Biphenyl-4-yl-3-cyclopentyl-propionyl)-3-methyl ureaYield 14%

Conditions

Temperature
25 °C

Procedure

A mixture of 2-biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester (987.4 mg, 3.20 mmol) and methyl urea (948.7 mg, 12.80 mmol) was treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 18 mL, 12.80 mmol). The resulting reaction mixture was then heated under reflux for 19 h. The reaction mixture was allowed to cool to 25° C. and then filtered through celite. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded 1-(2-biphenyl-4-yl-3-cyclopentyl-propionyl)-3-methyl urea (152.5 mg, 14%) as a white solid: mp 195-197° C.; EI-HRMS m/e calcd for C22H26N2O2 (M+) 350.1994, found 350.2004.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 19 h
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b1aa4e9188be4492b0f1af60a835595d
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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