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

HRID 1935267Notes

Reaction equation

HRID 1935267 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.[NH2:24][C:25]([NH2:27])=[O:26].C[O-].[Mg+2].C[O-].CO>>[C:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:16][C:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([NH:24][C:25]([NH2:27])=[O:26])=[O:23])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1176UreaHCID 164537Methanol, magnesium salt (2:1)HCID 674835462-Biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester

Product 1

HCID 10131862(2-Biphenyl-4-yl-3-cyclopentyl-propionyl) ureaYield 15%

Conditions

Temperature
25 °C

Procedure

A mixture of 2-biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester (415.5 mg, 1.35 mmol) and urea (202.3 mg, 3.37 mmol, 2.5 equiv) was treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 7.7 mL, 5.39 mmol). The resulting reaction mixture was then heated under reflux for 23 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 then 1/1 hexanes/ethyl acetate) afforded (2-biphenyl-4-yl-3-cyclopentyl-propionyl) urea (67.8 mg, 15%) as a white solid: mp 184-185° C.; FAB-HRMS m/e calcd for C21H24N2O2 (M+H)+ 337.1917, found 337.1924.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 23 h
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0794f956fcf042cabc1b07a33b403813
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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