Hydrogen Peroxide → HCID 178453573, compound

HRID 2389177Notes

Reaction equation

HRID 2389177 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C@:8]([CH3:32])([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:23]3)[CH:17]=2)[CH:12]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].N1C=NN=N1.C(N(CC)[P:42]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])C.[OH:55]O>O1CCCC1>[C:1]([O:5][C:6](=[O:33])[NH:7][C@:8]([CH3:32])([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][C@H:22]3[CH2:23][CH2:24][C@H:25]([C:28]([F:30])([F:31])[F:29])[CH2:26][CH2:27]3)[CH:17]=2)[CH:12]=1)[CH2:9][O:10][P:42]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:55])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 178418441HCID 178418441, compoundHCID 178453528HCID 178453528, compound

Product 1

HCID 178453573HCID 178453573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {(R)-2-Hydroxy-1-methyl-1-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-ethyl}-carbamic acid tert-butyl ester (172 mg, 0.000368 mol) and 1H-tetrazole (0.255 g, 0.00364 mol, ChemPacific) in tetrahydrofuran (3.00 mL, Acros) was added di-tert-butyl N,N-diethylphosphoramidite (512 μL, 0.00184 mol, Aldrich) and the reaction was stirred at rt for 16 hours. Hydrogen peroxide (250 μL, 0.0024 mol, Aldrich) was added and the reaction was stirred for 1.5 hours. The reaction was then quenched with 10% NaS2O3 in saturated sodium bicarbonate, extracted with EtOAc, washed with saturated sodium chloride and then dried with Na2SO4. The drying agent was filtered and the organic layer was concentrated in vacuo. The crude product was taken up in DCM and purified using silica gel chromatography (0-100% ethyl acetate in hexanes). Isolated was the product (Rf=0.52 in 1:1 hexanes/ethyl acetate) in 107.8 mg yield (44%).

Workup

  1. stirringthe reaction was stirred for 1.5 hours
  2. customThe reaction was then quenched with 10% NaS2O3 in saturated sodium bicarbonate
  3. extractionextracted with EtOAc
  4. washwashed with saturated sodium chloride
  5. dry with materialdried with Na2SO4
  6. filtrationThe drying agent was filtered
  7. concentrationthe organic layer was concentrated in vacuo
  8. custompurified
  9. customIsolated
  10. customyield (44%)

Sources & evidence

ORD record
ord-376ea30be3be41f6a4e4acdda9b92500
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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