Trifluoroacetic acid → HCID 86600997, compound

HRID 1351308Notes

Reaction equation

HRID 1351308 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([C:28](=[O:30])[CH3:29])=[CH:11][C:12]=1[S:13](=[O:27])(=[O:26])[N:14]([CH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[OH:18])[CH3:15])(C)(C)C.FC(F)(F)C(O)=O>O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH:17]([OH:18])[CH2:16][N:14]([CH3:15])[S:13]([C:12]2[CH:11]=[C:10]([C:28](=[O:30])[CH3:29])[S:9][C:8]=2[NH2:7])(=[O:27])=[O:26])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69413899HCID 69413899, compound

Product 1

HCID 86600997HCID 86600997, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(5-Acetyl-3-{[2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-sulfamo yl}-thiophene-2-yl)carbamic acid t-butyl ester (1.3 g) was added to trifluoroacetic acid (10 mL). After stirred for 10 minutes at room temperature, water was added to the residue that was evaporated in vacuo, and the pH of saturated sodium bicarbonate was adjusted to 11. The solution was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride water, whereafter this solution was dried with anhydrous magnesium sulfate. The solid obtained by passing through a short column of NH-silica gel and evaporating the solvent at reduced pressure was washed with ethyl acetate, and the title compound (713 mg) was obtained as an ocher solid.

Workup

  1. customwas evaporated in vacuo
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated sodium chloride water, whereafter this solution
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. customThe solid obtained
  6. customevaporating the solvent at reduced pressure
  7. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-c193a6faa8c34eba8a3a7a1eaed669d9
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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