Trifluoroacetic acid → HCID 45786769, compound

HRID 602176Notes

Reaction equation

HRID 602176 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][O:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)[CH2:16]1)=O)(C)(C)C>ClCCl>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[O:22][CH2:21][CH:17]1[CH2:18][CH2:19][CH2:20][NH:15][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58992705HCID 58992705, compound

Product 1

HCID 45786769HCID 45786769, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to 1-tert-butoxycarbonyl-3-[(benzothiazol-2-yl)oxymethyl]piperidine (460 mg, 1.32 mmol) in dichloromethane (2 mL). The mixture was stirred at room temperature for 3 hours. Subsequently, the solvent was evaporated and water was added to the residue, followed by a 1 mol/L aqueous sodium hydroxide solution to make the mixture basic. The mixture was then extracted with ethyl acetate and the extract washed with brine. The washed product was dried over magnesium sulfate and the solvent was evaporated to give 297 mg (91%) of the desired compound as a colorless oil.

Workup

  1. customSubsequently, the solvent was evaporated
  2. additionwater was added to the residue
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialThe washed product was dried over magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e9dd460abfa244128d6e78186845dc09
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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