Hydrogen Peroxide → HCID 58109163, compound

HRID 2037486Notes

Reaction equation

HRID 2037486 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[CH2:28])=[CH:23][CH:22]=2)[CH3:20])[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.[OH2:35].[OH-].[Na+].OO>C1COCC1.Cl>[OH:35][CH2:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([C@@H:19]([N:15]2[CH2:14][CH2:13][C@:12]([CH2:11][CH2:10][CH2:9][OH:8])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:17][C:16]2=[O:18])[CH3:20])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 58109435HCID 58109435, compound

Product 1

HCID 58109163HCID 58109163, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (20 mg, 0.042 mmol) in dry THF (10 mL) was added BH3 THF (0.5 ml, 0.5 mmol) dropwise at 0° C. After stirring for 2 h at rt, the mixture was cooled to 0° C., and H2O (0.5 mL), 3 M aqueous NaOH (0.5 mL) and 30% H2O2 (0.5 mL) were added successively added. The mixture was stirred overnight at rt. The mixture was diluted with 1 M HCl, and the pH of the mixture was adjusted to 6-7 with 1 M HCl. The layers were separated, and the aqueous phase was extracted with EtOAc (3×5 mL). The combined organic layer was washed with a saturated aqueous NaHCO3 solution (5 mL) and brine (5 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by TLC and preparative HPLC to afford (R)-3-((S)-1-(4-(2-hydroxyethyl)phenyl)ethyl)-6-(3-hydroxy propyl)-6-phenyl-1,3-oxazinan-2-one (7.02 mg, 20%). LC-MS Method 2 tR=1.757, min, m/z=406.2; 1H NMR (CDCl3): 1.31 (m, 1H), 1.47 (d, 3H), 1.68 (m, 1H), 1.89 (m, 2H), 2.18 (m, 2H), 2.70 (m, 1H), 2.83 (m, 1H), 3.49 (m, 2H), 3.71 (m, 2H), 5.58 (m, 1H), 6.75 (m, 2H), 6.88 (m, 2H), 7.23 (m, 5H).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. additionadded
  3. stirringThe mixture was stirred overnight at rt
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×5 mL)
  6. washThe combined organic layer was washed with a saturated aqueous NaHCO3 solution (5 mL) and brine (5 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto give the crude product, which
  10. customwas purified by TLC and preparative HPLC

Sources & evidence

ORD record
ord-fda7d88af4114a8c87d0ca58c3acc795
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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