Hydrogen Peroxide → HCID 69267907, compound

HRID 132632Notes

Reaction equation

HRID 132632 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][C@@H:8]([C:20](N1[C@H](C)[C@@H](C2C=CC=CC=2)OC1=O)=[O:21])[CH2:9][C@H:10]([CH3:19])[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].OO.S([O-])([O-])=[O:42].[Na+].[Na+]>O.C1COCC1>[C:1]([O:5][C:6](=[O:35])[CH2:7][C@H:8]([CH2:9][C@H:10]([CH3:19])[CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[C:20]([OH:21])=[O:42])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 69267185HCID 69267185, compound

Product 1

HCID 69267907HCID 69267907, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with 4.13 g (8.50 mmol) of (5R,3S)-7-cyclohexyl-5-methyl-3-((4R,5R)-4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-heptanoic acid tert-butyl ester, 100 mL of THF, 25 mL of water, and the resulting mixture was cooled in a 0° C. bath. To this solution was added 0.57 g (13.6 mmol) of lithium hydroxide monohydrate and 3.48 mL (34 mmol) of 30% hydrogen peroxide. The mixture was stirred for 2.5 hours. The reaction was quenched by the addition of 4.29 g (34 mmol) of sodium sulfite in 26 mL water. The mixture was allowed to warm to room temperature and stirred overnight. The THF was removed under reduced pressure and the remaining material was further diluted with water. The water layer was made acidic by the slow addition of conc. HCl aq. The aqueous layer was extracted with dichloromethane. The organic layers were dried with magnesium sulfate. The resulting oil was purified by column chromatography (eluent 3:1 hexanes:ethyl acetate). This gave 2.19 g (79% yield) of a clear oil: 1H NMR (400 MHz, CDCl3) δ ppm 0.88 (m, 5H) 1.17 (m, 10H) 1.43 (s, 10H) 1.68 (m, 7H) 2.35 (dd, J=16.35, 5.37 Hz, 1H) 2.60 (m, 1H) 2.87 (m, J=9.09, 9.09, 5.61, 5.49 Hz, 1H). MS (APCI) m+1/z is inconclusive.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe THF was removed under reduced pressure
  4. additionthe remaining material was further diluted with water
  5. additionThe water layer was made acidic by the slow addition of conc. HCl aq. The aqueous layer
  6. extractionwas extracted with dichloromethane
  7. dry with materialThe organic layers were dried with magnesium sulfate
  8. customThe resulting oil was purified by column chromatography (eluent 3:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-77318945854e4613ba559f5e93a614d2
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

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