Hydrogen Peroxide → HCID 50905738, compound

HRID 1422651Notes

Reaction equation

HRID 1422651 reaction equation
[CH3:1][C:2]1([CH2:5][C:6]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:11][C:10](=[O:12])[N:9]([C:13]([C:16]3[N:17]=[N:18][N:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:20]=3)([CH3:15])[CH3:14])[CH2:8][CH2:7]2)[CH2:4][O:3]1.O.OO.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1>[OH:3][C:2]([CH3:4])([CH3:1])[CH2:5][C:6]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:11][C:10](=[O:12])[N:9]([C:13]([C:16]2[N:17]=[N:18][N:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:20]=2)([CH3:15])[CH3:14])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 24477Sodium ThiosulfateHCID 86669142HCID 86669142, compound

Product 1

HCID 50905738HCID 50905738, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of crude 6-((2-methyloxiran-2-yl)methyl)-6-phenyl-3-(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)-1,3-oxazinan-2-one (8.4 mg, 0.018 mmol) in dry THF (1 mL) was cooled in an ice bath and 1 M LiEt3BH in THF (0.1 mL, 0.1 mmol) was added. The mixture was stirred for 45 min in the ice bath. Water (1 mL) and 30% H2O2 (0.2 mL) were added. The mixture was stirred for 0.5 h and solid Na2S2O3 (˜200 mg) was added. The mixture was stirred for 0.5 h and applied to a 10-mL ChemElut cartridge. The cartridge was eluted with EtOAc (50 mL) and the eluate was concentrated to leave a residue which was purified by prep HPLC to afford the title compound (2.5 mg, 42% over 2 steps). LC-MS Method 1 tR=1.57 min, m/z=435.

Workup

  1. stirringThe mixture was stirred for 0.5 h
  2. washThe cartridge was eluted with EtOAc (50 mL)
  3. concentrationthe eluate was concentrated
  4. customto leave a residue which
  5. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-e9db1c8165da4163a47f65a53a03eac2
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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