Hydrogen Peroxide → HCID 67530779, compound

HRID 2389113Notes

Reaction equation

HRID 2389113 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([C@:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:27][OH:28])[CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=NN=N1.[O:43]1CCCC1.C(N(CC)[P:51]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])C.OO>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([C@:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:27][O:28][P:51]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:43])[CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 67531733HCID 67531733, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 67530779HCID 67530779, compoundYield 101.9%

Procedure

To a solution of (R)-tert-butyl 2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-1-hydroxypropan-2-ylcarbamate (20.0 mg, 0.0000388 mol) and 1H-tetrazole (30.4 mg, 0.000434 mol) in tetrahydrofuran (2 mL, 0.02 mol) was added di-tert-butyl N,N-diethylphosphoramidite (60.1 μL, 0.000216 mol) at room temperature. The resulting mixture was stirred at room temperature overnight, then hydrogen peroxide (180 μL, 0.0017 mol) was added and the mixture was stirred at room temperature for 1 h. The reaction was quenched with saturated. Na2S2O3, then extracted with EtOAc, and dried over Na2SO4. The residue was chromatographed with MeOH—CH2Cl2 (0-20%) to give (R)-tert-butyl 2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-1-(di-tert-butoxyphosphoryloxy)propan-2-ylcarbamate as a gel (28 mg, 100%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. customThe reaction was quenched with saturated
  3. extractionNa2S2O3, then extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe residue was chromatographed with MeOH—CH2Cl2 (0-20%)

Sources & evidence

ORD record
ord-1687eed6fcdc48edb528db590e21c3b0
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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