Sulfuric Acid → {2-[2-(3-Chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-acetic acid methyl ester

HRID 1355043Notes

Reaction equation

HRID 1355043 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:27])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[S:9][CH:10]=1)C.S(=O)(=O)(O)O>CO>[CH3:1][O:3][C:4](=[O:28])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:27])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[S:9][CH:10]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 23394572{2-[2-(3-Chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester

Product 1

HCID 20707087{2-[2-(3-Chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-acetic acid methyl esterYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {2-[2-(3-chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester (prepared as in Example 28A, 177.2 mg, 0.42 mmol) in methanol (15 mL) was treated with a catalytic amount of sulfuric acid. The reaction mixture was heated under reflux for 40 h. The reaction was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 70/30 hexanes/ethyl acetate) afforded {2-[2-(3-chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-acetic acid methyl ester (104.4 mg, 60.9%) as a clear oil: EI-HRMS m/e calcd for C20H23ClN2O3S (M+) 406.1117, found 406.1118.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 40 h
  3. concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record
ord-cdaac2ff09e64c7eaf273ce3c2959dd5
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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