Hydrochloric Acid → HCID 18739628, compound

HRID 1935230Notes

Reaction equation

HRID 1935230 reaction equation
[CH:1]1([CH2:6][CH:7]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:34]O>>[CH3:34][O:18][C:17](=[O:19])[CH2:16][C:14]1[N:15]=[C:11]([NH:10][C:8](=[O:9])[CH:7]([C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)[CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[S:12][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22467902{2-[3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazol-4-yl}-acetic acid

Product 1

HCID 18739628HCID 18739628, compoundYield 61%

Procedure

A solution of {2-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazol-4-yl}-acetic acid (prepared in Example 16, 80 mg, 0.18 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]-thiazol-4-yl}-acetic acid methyl ester (50 mg, 61%) as a yellow oil: EI-HRMS m/e calcd for C26H28N2O4S (M+) 464.1770, found 464.1769.

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-2978fb1632dd425e9645fa592c313a74
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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