Hydrochloric Acid → 2-[3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester

HRID 1935227Notes

Reaction equation

HRID 1935227 reaction equation
[CH:1]1([CH2:6][CH:7]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:33]O>>[CH3:33][O:17][C:16]([C:14]1[N:15]=[C:11]([NH:10][C:8](=[O:9])[CH:7]([C:19]2[CH:20]=[CH:21][C:22]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:23][CH:24]=2)[CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[S:12][CH:13]=1)=[O:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 224679272-[3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazole-4-carboxylic acid

Product 1

HCID 187396292-[3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl esterYield 39%

Procedure

A solution of 2-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazole-4-carboxylic acid (100 mg, 0.23 mmol) in methanol (10 mL) was treated with concentrated hydrochloric acid (1 mL) and then heated under reflux for 16 h. At this time, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (10 mL) and then washed with water (5 mL). The aqueous layer was further extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 2-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (40 mg, 39%) as a white foam: EI-HRMS m/e calcd for C25H26N2O4S (M+) 450.1613, found 450.1615.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. concentrationAt this time, the reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  5. washwashed with water (5 mL)
  6. extractionThe aqueous layer was further extracted with ethyl acetate (3×5 mL)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1dc13f71cdcf4c82a4238bce6bb93829
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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