Trifluoroacetic acid → HCID 68882130, compound

HRID 1829715Notes

Reaction equation

HRID 1829715 reaction equation
O[C:2]1([C:18]2[C:22]([CH3:23])=[C:21]([Br:24])[S:20][C:19]=2[F:25])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C([SiH](CC)CC)C>[Br:24][C:21]1[S:20][C:19]([F:25])=[C:18]([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]2)[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68884233HCID 68884233, compound

Product 1

HCID 68882130HCID 68882130, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Procedure

To an ice-cooled, rapidly stirred slurry of 4-hydroxy-4-(5-bromo-2-fluoro-4-methylthiophenyl)-N-Cbz-piperidine (7.82 g) in triethylsilane (19.7 g) was slowly added tri-fluoroacetic acid (18.6 g). When addition was complete the mixture was warmed to room temperature and stirred overnight (18 h). At the end of this period the mixture was poured into 100 mL saturated NaHCO3 and extracted with DCM. Extracts were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to give an oil. The product was purified by chromatography on silica (7:3, hexane:EtOAc) to give 5.18 g of an oil; MS m/z 438 (M+); 1H NMR (CDCl3) δ 7.45-7.30 (m), 7.25 (d), 6.80 (d), 5.15 (s), 4.50-4.20 (m), 3.11-2.80 (m), 1.90-1.48 (m).

Workup

  1. additionWhen addition
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customThe product was purified by chromatography on silica (7:3, hexane:EtOAc)

Sources & evidence

ORD record
ord-2da6e763cb7b44e4aa1208ea37c341e5
Source dataset
uspto-grants-2006_06
Patent number
US07064136B2

Reaction notes

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