Methanol → HCID 9905747, compound

HRID 430110Notes

Reaction equation

HRID 430110 reaction equation
CO[C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[NH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C[O-].[Mg+2].C[O-].CO>>[Cl:17][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:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:18])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 164537Methanol, magnesium salt (2:1)HCID 54346252HCID 54346252, compound

Product 1

HCID 9905747HCID 9905747, compoundYield 61.9%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(3-chloro-phenyl)-3-cyclopentyl-propionic acid methyl ester (113 mg, 0.42 mmol) and 2-aminothiazole (84 mg, 0.84 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 2.4 mL, 1.69 mmol) was refluxed at 100° C. for 20 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 2-(3-chloro-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (87 mg, 53%) as a white solid: mp 138.8-141.2° C.; EI-HRMS m/e calcd for C17H19ClN2OS (M+) 334.0906, found 334.0907.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-6ad8ed2afeba42f19056fba9f0f38851
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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