Sulfuric Acid → HCID 20707093, compound

HRID 398467Notes

Reaction equation

HRID 398467 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][C:23]([Cl:26])=[CH:22][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:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=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 54559234HCID 54559234, compound

Product 1

HCID 20707093HCID 20707093, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[2-(4-chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazole-4-carboxylic acid ethyl ester (prepared as in Example 31(B)(a), 105 mg, 0.25 mmol) in methanol (10 mL) was treated with a catalytic amount of sulfuric acid. The reaction mixture was heated under reflux for 68 h. The reaction was concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μm, 60 Å, 25 cm×23 cm ID, 75/25 heptane/ethyl acetate) afforded 2-[2-(4-chloro-phenyl)-3-cyclopentyl-propionylamino]-thiazole-4-carboxylic acid methyl ester (41.3 mg, 40.7%) as a white solid: mp 156-157° C.; EI-HRMS m/e calcd for C19H21ClN2O3S (M+) 392.0961, found 392.0956.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 68 h
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-1c438598212248128ad4ce237b0c9820
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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