Water → HCID 178501144, compound

HRID 2272654Notes

Reaction equation

HRID 2272654 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)=[O:7].[F:18][C:19]([Si](C)(C)C)([F:21])[F:20].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1.C(OCC)(=O)C>[F:18][C:19]([F:21])([F:20])[C:6]([C@H:8]1[CH2:9][CH2:10][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13]1)([OH:7])[C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 552549(Trifluoromethyl)trimethylsilaneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 178501142HCID 178501142, compound

Product 1

HCID 178501144HCID 178501144, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of methyl trans-4-(thiazole-2-carbonyl)cyclohexanecarboxylate (1.1 g, 4.34 mmol) in THF (20 mL) at 0° C. was added trifluoromethyltrimethylsilane (1.286 mL, 8.68 mmol). Tetrabutylammonium fluoride trihydrate (1M in THF, 17.37 mL, 17.37 mmol) was added slowly maintaining the temperature at 0° C. The reaction was allowed to stir for 1 hr and then water (30 mL) and ethyl acetate (30 mL) was added to quench the reaction. The organic layer was removed, washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-20% ethyl acetate in hexane) to afford methyl trans-4-[2,2,2-trifluoro-1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate. MS ESI calcd. for C13H17F3NO3S [M+H]+ 324. found 324. 1H NMR (500 MHz, CDCl3) δ 7.79 (d, J=3.2 Hz, 1H), 7.49 (d, J=3.2 Hz, 1H), 4.77 (s, 1H), 3.65 (s, 3H), 2.40 (m, 1H), 2.30-1.90 (m, 3H), 1.50-1.20 (m, 6H).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was removed
  4. washwashed with brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-fa967abc853b49f9bea3e37918c175db
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

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