Hydrochloric Acid → 2-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide

HRID 854810Notes

Reaction equation

HRID 854810 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:18][CH:19]2[CH2:23][CH2:22][C:21]3(OCCC[O:24]3)[CH2:20]2)[C:10]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:18][CH:19]2[CH2:23][CH2:22][C:21](=[O:24])[CH2:20]2)[C:10]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21958973HCID 21958973, compound

Product 1

HCID 100000032-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-N-thiazol-2-yl-propionamideYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude 2-(3,4-dichloro-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-N-thiazol-2-yl-propionamide (768.5 mg, 1.74 mmol) in tetrahydrofuran (8.7 mL) and a 5% aqueous hydrochloric acid solution (3.9 mL) was stirred at 25° C. for 64 h. The resulting reaction solution was concentrated in vacuo to remove tetrahydrofuran and then diluted with ethyl acetate (100 mL). The organic layer was washed with a 1% aqueous hydrochloric acid solution (50 mL), water (50 mL) and a saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50% ethyl acetate/hexanes) afforded 2-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide (481.9 mg, 47% over 2 steps) as a white solid: mp 146-148° C.; (ES)+-HRMS m/e calcd for C17H16C12N2O2S (M+H)+ 383.0383. found 383.0385.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated in vacuo
  3. customto remove tetrahydrofuran
  4. additiondiluted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with a 1% aqueous hydrochloric acid solution (50 mL), water (50 mL)
  6. dry with materiala saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3aff16ce1a649c4adbc60e2f0e478a2
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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