Trifluoromethanesulfonic acid → HCID 69097842, compound

HRID 1024121Notes

Reaction equation

HRID 1024121 reaction equation
OS([C:5]([F:8])(F)F)(=O)=O.[CH3:9][O:10][C:11]([C:13]1[S:14][C:15]([CH2:18][CH2:19][CH2:20][C@H:21]2[CH2:25][CH2:24]C([Sn](C)(C)C)=[C:22]2[C:30]2[CH:35]=[CH:34][C:33]([CH:36]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=3)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:32][CH:31]=2)=[CH:16][CH:17]=1)=[O:12].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>C(Cl)Cl.[Al]>[CH3:9][O:10][C:11]([C:13]1[S:14][C:15]([CH2:18][CH2:19][CH2:20][C@H:21]2[CH2:25][CH2:24][C:5]([F:8])=[C:22]2[C:30]2[CH:31]=[CH:32][C:33]([CH:36]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=3)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:34][CH:35]=2)=[CH:16][CH:17]=1)=[O:12]

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 69098020HCID 69098020, compound

Product 1

HCID 69097842HCID 69097842, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent4×HCID 5359268AluminumSolvent

Procedure

An analogous procedure to that described in Marcus A. Tius and Joel K. Kawakami Tetrahedron 1995, 51, 3997 was used. A solution of triflic acid (37 μL, 0.42 mmol) in 0.37 mL CH2Cl2 was added to a mixture of Ag2CO3 (83 mg, 0.30 mmol) in 2.8 mL CH2Cl2 and the flask was covered in aluminum foil. After 30 min., a solution of 57 (ca. 0.38 mmol, directly from above) and 2,6-di-tert-butyl-4-methylpyridine (49 mg, 0.24 mmol) in 2.8 mL CH2Cl2 was added dropwise by cannula, rinsing with 1 mL CH2Cl2. At this time, a solution of XeF2 (82 mg, 0.48 mmol) in 5.5 mL CH2Cl2 was added by cannula. The reaction was stirred for 1 h and then was quenched by addition of 10 mL saturated NaHCO3 solution. The resulting mixture was extracted with CH2Cl2 (3×30 mL) and the combined solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on a Teledyne Isco Combiflash unit (40 g silica gel column, 0%→100% ethyl acetate/hexanes) followed by HPLC (Phenomenex 50 mm×250 mm silica gel column, 5% ethyl acetate/hexanes) to give the title compound (12 mg, 5%).

Workup

  1. washrinsing with 1 mL CH2Cl2
  2. customwas quenched by addition of 10 mL saturated NaHCO3 solution
  3. extractionThe resulting mixture was extracted with CH2Cl2 (3×30 mL)
  4. dry with materialthe combined solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on a Teledyne Isco Combiflash unit (40 g silica gel column, 0%→100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-251ce32f64454ce4b07d8647e46652a0
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

Loading…