Methanol → 1-[3-Cyclopentyl-2-(4-nitro-phenyl)-propionyl]-3-methyl-urea

HRID 1860121Notes

Reaction equation

HRID 1860121 reaction equation
C(O[C:4](=[O:21])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[CH3:22][NH:23][C:24]([NH2:26])=[O:25].C[O-].[Mg+2].C[O-].CO>>[CH:7]1([CH2:6][CH:5]([C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[C:4]([NH:26][C:24]([NH:23][CH3:22])=[O:25])=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 114718493-Cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester

Product 1

HCID 120444541-[3-Cyclopentyl-2-(4-nitro-phenyl)-propionyl]-3-methyl-ureaYield 13.2%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester (1.27 g, 4.36 mmol) and methyl urea (647 mg, 8.73 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 9.36 mL, 6.54 mmol) was refluxed at 100° C. for 8.5 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(4-nitro-phenyl)-propionyl]-3-methyl-urea (183.6 mg, 13.2%) as a white solid: mp 179-183° C.; EI-HRMS m/e calcd for C16H21N3O4(M+) 319.1532, found 319.1527.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-05706b9ec4744fb199042f56ce6bca39
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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