Trifluoroacetic acid → HCID 59610053, compound

HRID 1889184Notes

Reaction equation

HRID 1889184 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:40])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22][C:21]([N:23](C(OC(C)(C)C)=O)CC3C=CC(OC)=CC=3)=[N:20][CH:19]=2)=[CH:14][CH:13]=1)[CH3:9]>>[CH2:8]([O:10][C:11](=[O:40])[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[S:22][C:21]([NH2:23])=[N:20][CH:19]=2)=[CH:16][CH:17]=1)[CH3:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59610043HCID 59610043, compound

Product 1

HCID 59610053HCID 59610053, compound

Procedure

Trifluoroacetic acid (5 ml) was added to 4-{2-[tert-Butoxycarbonyl-(4-methoxy-benzyl)-amino]-thiazol-5-yl}-benzoic acid ethyl ester (300 mg, 0.64 mmol) at room temperature and reaction mixture was refluxed for 5 hrs. Trifluoroacetic acid was removed on rotavapour. The residue was taken in water (10 ml) and ethyl acetate (15 ml) and basified this with sodium bicarbonate, layers were separated, and aq. layer was re-extracted with ethyl acetate (15 ml). The combined organic layer was washed with brine (15 ml) and dried over anhydrous sodium sulfate. Solvent was evaporated on rotavapour to get the solid product. The crude material was used for the next step with out any further purification,(150 mg).

Workup

  1. customreaction mixture
  2. temperaturewas refluxed for 5 hrs
  3. customTrifluoroacetic acid was removed on rotavapour
  4. customwere separated
  5. extractionaq. layer was re-extracted with ethyl acetate (15 ml)
  6. washThe combined organic layer was washed with brine (15 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customSolvent was evaporated on rotavapour
  9. customto get the solid product
  10. customThe crude material was used for the next step with out any further purification,(150 mg)

Sources & evidence

ORD record
ord-90de1b3fe7384890a2ecddf97f9df9cc
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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