Methanol → HCID 10294433, compound

HRID 1935274Notes

Reaction equation

HRID 1935274 reaction equation
CO[C:3](=[O:27])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[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.[CH3:28][NH:29][C:30]([NH2:32])=[O:31].C[O-].[Mg+2].C[O-].CO>>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[C:3]([NH:32][C:30]([NH:29][CH3:28])=[O:31])=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 67483520HCID 67483520, compound

Product 1

HCID 10294433HCID 10294433, compoundYield 35%

Conditions

Temperature
25 °C

Procedure

A mixture of 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid methyl ester (196.5 mg, 0.548 mmol) and methyl urea (121.8 mg, 1.64 mmol) was treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 3.1 mL, 2.19 mmol). The resulting reaction mixture was then heated under reflux for 24 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, 9/1 hexanes/ethyl acetate then 3/1 to 1/1 hexanes/ethyl acetate gradient elution) afforded 1-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionyl]-3-methyl urea (76.9 mg, 35%) as a white foam: mp 85-88° C.; EI-HRMS m/e calcd for C26H28N2O2 (M+) 400.2151, found 400.2150.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 24 h
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. washFlash chromatography (Merck Silica gel 60, 230-400 mesh, 9/1 hexanes/ethyl acetate then 3/1 to 1/1 hexanes/ethyl acetate gradient elution)

Sources & evidence

ORD record
ord-99f0285c2e624a4cbd6ecb355da80d65
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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