Sulfuric Acid → HCID 20707090, compound

HRID 1355044Notes

Reaction equation

HRID 1355044 reaction equation
[CH2:1]([O:3][C:4]([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)=[O:5])C.S(=O)(=O)(O)O>CO>[CH3:1][O:3][C:4]([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)=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 53722820HCID 53722820, compound

Product 1

HCID 20707090HCID 20707090, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[2-(3-chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazole-4-carboxylic acid ethyl ester (prepared as in Example 28(B)(a), 94.5 mg, 0.23 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, 75/25 hexanes/ethyl acetate) afforded 2-[2-(3-chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazole-4-carboxylic acid methyl ester (36.8 mg, 40.3%) as a white solid: mp 95–98° C.; EI-HRMS m/e calcd for C19H21ClN2O3S (M+) 392.0961, found 392.0989.

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-df23f9e9fb45421bbc11e10fe420c316
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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