Methanol → HCID 21959053, compound

HRID 2214064Notes

Reaction equation

HRID 2214064 reaction equation
CO[C:3](=[O:26])[CH:4]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[CH3:27][NH:28][C:29]([NH2:31])=[O:30].C[O-].[Mg+2].C[O-].CO>>[Cl:25][C:20]1[CH:19]=[C:18]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH:7]2[O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:3]([NH:31][C:29]([NH:28][CH3:27])=[O:30])=[O:26])[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 674821332-(3,4-Dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester

Product 1

HCID 21959053HCID 21959053, compoundYield 11.8%

Conditions

Temperature
110 °C

Procedure

2-(3,4-Dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester (400 mg, 0.99 mmol) and methylurea (110.7 mg, 1.49 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. %, 2.85 mL, 1.99 mmol) was heated under reflux at 110° C. for 6 h. The reaction mixture was then concentrated in vacuo and filtered through a plug of celite (ethyl acetate as eluent). Flash chromatography (Merck Silica gel 60, 230–400 mesh, 100% ethyl acetate) afforded 1-{2-(3,4-dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionyl}-3-methyl-urea (52 mg, 11.8%) as a white solid: mp 68–70° C.; FAB-HRMS m/e calcd for C21H28Cl2N2O4 (M+H)+ 443.1504, found 443.1499.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. filtrationfiltered through a plug of celite (ethyl acetate as eluent)

Sources & evidence

ORD record
ord-9d9b81079ef84ae090e5a53ba754c92e
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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