Trifluoroacetic acid → HCID 67241221, compound

HRID 2239677Notes

Reaction equation

HRID 2239677 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([N:12]1[C:16](=[O:17])[C:15]([NH:18][CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[C:14]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[S:13]1(=[O:39])=[O:38])([CH3:11])([CH3:10])[CH3:9].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:8]([N:12]1[C:16](=[O:17])[C:15]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[C:14]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[S:13]1(=[O:39])=[O:38])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 11568879HCID 11568879, compound

Product 1

HCID 67241221HCID 67241221, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 ml) was added to a solution of tert-butyl 4-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]piperidine-1-carboxylate (Example 86) (2.138 g, 4.612 mmol) in DCM (20 ml) and the mixture was stirred at rt for 80 mins. TFA (1 mil) was added and the reaction mixture was stirred for 18 h. The reaction mixture was basified by addition of saturated aqueous NaHCO3. The organic layer was separated and the aqueous phase was extracted with DCM. The combined organic phases were washed with brine, and evaporated to give the title compound (1.630 g, 97%) as a solid. 1H NMR (500 MHz, CDCl3): δ 7.54-7.50 (m, 2H), 7.50-7.40 (m, 3H), 5.20 (d, 1H), 3.08-2.92 (m, 3H), 2.19 (dt, 2H), 1.74 (s, 9H), 1.72-1.46 (m, 2H), 1.36-1.24 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 159.9, 134.0, 131.8, 130.1, 128.9, 125.3, 107.1, 61.8, 50.2, 44.7, 33.1, 27.9; Mass Spectrum: M+H+ 364.

Workup

  1. stirringthe reaction mixture was stirred for 18 h
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with DCM
  4. washThe combined organic phases were washed with brine
  5. customevaporated

Sources & evidence

ORD record
ord-23cd7e367b06445d80e3fb32c74f37ff
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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