Sulfuric Acid → HCID 20707090, compound

HRID 398464Notes

Reaction equation

HRID 398464 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-b61d48acd4f44279bd3579ba543f8a8e
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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