Methanol → HCID 12044452, compound

HRID 1860116Notes

Reaction equation

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

Participants

Reactant 4

HCID 887Methanol

HCID 11719Methylurea

HCID 164537Methanol, magnesium salt (2:1)

HCID 54098154HCID 54098154, compound

Product 1

HCID 12044452HCID 12044452, compoundYield 9.4%

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-cyclopentyl-2-(3,4-difluoro-phenyl)-propionic acid methyl ester (1.65 g, 6.14 mmol) and methyl urea (683 mg, 9.22 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 16.6 mL, 12.3 mmol) was refluxed at 100° C. for 8 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-[3-cyclopentyl-2-(3,4-difluoro-phenyl)-propionyl]-3-methyl-urea (180 mg, 9.4%) as a white solid: mp 111-113° C.; EI-HRMS m/e calcd for C16H20F2N2O2 (M+) 310.1493, found 310.1499.

Workup

concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-5523b8d9a40c4d1382d5cc78f6cb2e65
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528543B1

Reaction notes

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