Trifluoroacetic acid → HCID 67241221, compound

HRID 2422078Notes

Reaction equation

HRID 2422078 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-f3b206112a5b4fd492c4ccd5963d7b1e
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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