Hydrogen Peroxide → HCID 71006908, compound

HRID 403358Notes

Reaction equation

HRID 403358 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:18][CH2:17][C@@H:16]([OH:19])[C:12]2[N:13]=[CH:14][S:15][C:11]=2[C@H:10]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].OO.C(=O)([O-])[O-].[Na+].[Na+].[F:36][C:37](I)([F:39])[F:38].CS(C)=O>C1([Fe]C2C=CC=C2)C=CC=C1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:18][CH2:17][C@@H:16]([OH:19])[C:12]2[N:13]=[C:14]([C:37]([F:39])([F:38])[F:36])[S:15][C:11]=2[C@H:10]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 71006901HCID 71006901, compoundHCID 89158462HCID 89158462, compound

Product 1

HCID 71006908HCID 71006908, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 178420578HCID 178420578, compoundCatalyst

Procedure

Trifluoromethyliodide gas was bubbled through 4 mL of dimethylsulfoxide for 3 min at rt. In this way, approximately 0.9 g of trifluoromethyliodide was dissolved in this solution. Dicyclopentadienyliron(II) (21.9 mg, 0.114 mmol) and tert-butyl (4R,7S,8S)-7-(2,3-difluorophenyl)-4-hydroxy-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-8-ylcarbamate (45.3 mg, 0.114 mmol) was dissolved in 2 mL of the trifluoromethyliodide-dimethylsulfoxide solution described above. Hydrogen peroxide (0.012 mL, 0.114 mmol) was added to the reaction mixture. The reaction was stirred at rt for 1 h. Aqueous sodium carbonate was added and the reaction was extracted with ethyl acetate. The ethyl acetate layer was washed with water (2×) and dried (sodium sulfate). The product was purified by flash chromatography, eluting with ethyl acetate in hexane from 0 to 30% to 45% to give the desired product (12.5 mg, 24%): LCMS (M+H=465.08); 1H NMR (400 MHz, CHLOROFORM-d) δ 7.21-6.97 (m, 3H), 5.30-5.16 (m, 1H), 498-4.84 (m, 2H), 3.43-3.28 (m, 1H), 3.12-2.79 (m, 2H), 2.43-2.13 (m, 3H), 1.37-1.18 (m, 9H).

Workup

  1. customTrifluoromethyliodide gas was bubbled through 4 mL of dimethylsulfoxide for 3 min at rt
  2. dissolutionIn this way, approximately 0.9 g of trifluoromethyliodide was dissolved in this solution
  3. extractionthe reaction was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water (2×)
  5. dry with materialdried (sodium sulfate)
  6. customThe product was purified by flash chromatography
  7. washeluting with ethyl acetate in hexane from 0 to 30% to 45%

Sources & evidence

ORD record
ord-799ffb703c694210a092c50e109dba7d
Source dataset
uspto-grants-2014_06
Patent number
US08748429B2

Reaction notes

Loading…