Methanol → HCID 12044455, compound

HRID 1860123Notes

Reaction equation

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

Participants

Reactant 4

HCID 887Methanol

HCID 11719Methylurea

HCID 164537Methanol, magnesium salt (2:1)

HCID 53726727HCID 53726727, compound

Product 1

HCID 12044455HCID 12044455, compoundYield 62.4%

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-cyclopentyl-2-phenyl-propionic acid ethyl ester (1.70 g, 7.06 mmol) and methyl urea (1.04 mg, 14.13 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 130.3 mL, 21.18 mmol) was refluxed at 100° C. for 24 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-phenyl-propionyl)-3-methyl-urea (1.21 mg, 62.4%) as a white solid: mp 145-147° C.; EI-HRMS m/e calcd for C16H22N2O2 (M+) 274.1681, found 274.1682.

Workup

concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-ea76db2d934d48f385f8817fc8f2815a
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528543B1

Reaction notes

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