Methanol → HCID 10091453, compound

HRID 854778Notes

Reaction equation

HRID 854778 reaction equation
CO[C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[OH:11].[NH2:21][C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C[O-].[Mg+2].C[O-].CO>>[Cl:19][C:14]1[CH:13]=[C:12]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH:7]2[OH:11])[C:3]([NH:21][C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[O:20])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 164537Methanol, magnesium salt (2:1)HCID 674821962-(3,4-Dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester

Product 1

HCID 10091453HCID 10091453, compoundYield 55.1%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester (262.2 mg, 0.82 mmol) and 2-aminothiazole (165 mg, 1.65 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. % , 2.60 mL, 1.81 mmol) was heated to 100° C. for 18 h. At this time, the reaction mixture was cooled to 25° C. and filtered through a pad of celite (ethyl acetate as eluent). The filtrate was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 ethyl acetate/hexanes) afforded the 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-N-thiazol-2-yl-propionamide (174 mg, 54.6%) as a white solid: mp 86-88° C.; EI-HRMS m/e calcd for C17H18Cl2N2O2S (M+Na)+ 407.0358. found 407.0361.

Workup

  1. temperatureAt this time, the reaction mixture was cooled to 25° C.
  2. filtrationfiltered through a pad of celite (ethyl acetate as eluent)
  3. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-7e72569e038145958b944ef5321ce3ce
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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