Sodium Thiosulfate → HCID 178433054, compound

HRID 1036513Notes

Reaction equation

HRID 1036513 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:30]([F:33])([F:32])[F:31])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]2([CH2:28][OH:29])[CH2:26][O:25][C:24]([CH3:27])=[N:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)[P:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])C.N1C=NN=N1.ClC1C=CC=C(C(OO)=[O:63])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.C(=O)(O)[O-].[Na+]>[P:37]([O:29][CH2:28][C:22]1([C:17]2[CH:16]=[CH:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]4[CH2:7][CH2:6][C@H:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:9]4)[C:13]=3[C:30]([F:32])([F:33])[F:31])[CH:18]=2)[CH2:26][O:25][C:24]([CH3:27])=[N:23]1)([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:63]

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 178418441HCID 178418441, compoundHCID 178432969HCID 178432969, compound

Product 1

HCID 178433054HCID 178433054, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

{4-[6-(trans-4-tert-Butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol (227 mg, 0.000490 mol) was treated with di-tert-butyl N,N-diethylphosphoramidite (545 μL, 0.00196 mol, Aldrich), 1H-tetrazole (177 mg, 0.00253 mol, ChemPacific) in tetrahydrofuran (10.0 mL, Aldrich) overnight. m-Chloroperbenzoic acid (570 mg, 0.00198 mol) was added to a cooled solution (ice bath) and the reaction was stirred at room temperature for 1 hour. Sodium thiosulfate was added as a 10% solution in saturated sodium bicarbonate (10 mL) and the reaction stirred for 2 h. The reaction was evaporated. The mixture was partitioned between methylene chloride and water/saturated sodium bicarbonate. The organic layer was further washed once with water and then dried with magnesium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography on a column pre-treated with 1% triethylamine/methylene chloride, then eluted with 0-10% methanol in methylene chloride. Concentrating appropriate fractions gave the product in 234 mg yield (73%).

Workup

  1. stirringthe reaction stirred for 2 h
  2. customThe reaction was evaporated
  3. customThe mixture was partitioned between methylene chloride and water/saturated sodium bicarbonate
  4. washThe organic layer was further washed once with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography on a column
  9. additionpre-treated with 1% triethylamine/methylene chloride
  10. washeluted with 0-10% methanol in methylene chloride
  11. concentrationConcentrating appropriate fractions
  12. customgave the product in 234 mg
  13. customyield (73%)

Sources & evidence

ORD record
ord-ff8e66a39258493799a58a04a8723e06
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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