Methanol → HCID 18626613, compound

HRID 1860169Notes

Reaction equation

HRID 1860169 reaction equation
CO[C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([Cl:21])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.C(OC(=O)C(C1C=CC(S(C)(=O)=O)=C(Cl)C=1)CC1CCCC1)C.[CH3:46][NH:47][C:48]([NH2:50])=[O:49].CO>C[O-].[Mg+2].C[O-]>[Cl:21][C:13]1[CH:12]=[C:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([NH:50][C:48]([NH:47][CH3:46])=[O:49])=[O:22])[CH:16]=[CH:15][C:14]=1[S:17]([CH3:20])(=[O:18])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 53763168HCID 53763168, compoundHCID 54447124HCID 54447124, compound

Product 1

HCID 18626613HCID 18626613, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 164537Methanol, magnesium salt (2:1)Solvent

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester and 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid ethyl ester (268 mg) and methyl urea (110 mg, 1.5 mmol) in magnesium methoxide in methanol (7.4 wt %, 1.6 mL, 1.1 mmol) was heated to 100° C. for 8 h. At this time, the reaction was concentrated in vacuo. The residue was then dissolved in ethyl acetate (50 mL), filtered through a plug of silica gel, and washed with ethyl acetate (100 mL). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) afforded 1-[2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (55 mg, 19% yield) as a white foam: FAB-HRMS m/e calcd for C17H23ClN2O4S (M+H)+387.1145, found 387.1156.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. dissolutionThe residue was then dissolved in ethyl acetate (50 mL)
  3. filtrationfiltered through a plug of silica gel
  4. washwashed with ethyl acetate (100 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8809ed4042d04093a6caa6374db0f709
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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