Potassium Carbonate → HCID 131729387, compound

HRID 420313Notes

Reaction equation

HRID 420313 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH:23]([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])[C:19]([N+:32]([O-:34])=[O:33])=[C:18]([F:35])[CH:17]=2)[CH2:11]S[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O[O:38][S:39]([O-:41])=O.[K+].CC([O-])=O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH:23]([C:24]([F:25])([F:27])[F:26])[C:28]([F:29])([F:31])[F:30])[C:19]([N+:32]([O-:34])=[O:33])=[C:18]([F:35])[CH:17]=2)[CH2:11][S:39](=[O:41])(=[O:38])[CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 656671Sodium PyrosulfiteHCID 23707502Potassium hydroxy sulfiteHCID 72190739HCID 72190739, compound

Product 1

HCID 131729387HCID 131729387, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of {(3R,4S,5S)-5-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-benzyl]-4-hydroxy-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester (3.31 g, 6.0 mmol) in THF-H2O 1:1 (150 mL) was added oxone (7.6 g, 12.0 mmol). After stirring the reaction mixture for 2 h at 25° C., 2.5 g NaOAc and 3 g sodium metabisulfite were added. The reaction mixture was stirred for 0.5 h, basified with saturated aq. K2CO3-solution and the product was extracted with EtOAc. Combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound after chromatographic purification (Combi-Flash, 40 g silicagel, hexane-EtOAc 95:5 to EtOAc) as a colorless amorphous solid: TLC (toluene-THF 1:1) Rf=0.45; HPLC RtA=2.21 min; ESIMS [M+NH4]+=602; 1H NMR (400 MHz, CDCl3): δ 6.92 (d, 1H), 6.85 (s, 1H), 5.05 (m, 1H), 4.92 (d, 1H), 4.02 (m, 1H), 3.45 (m, 1H), 3.34 (m, 2H), 3.22 (dd, 1H), 3.18 (m, 1H), 2.94 (m, 1H), 2.82 (dd, 1H), 2.74 (dd, 1H), 2.52 (m, 1H), 1.43 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred for 0.5 h
  2. extractionthe product was extracted with EtOAc
  3. washCombined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3bb32d7be53a44ab95e4a983de469d18
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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