Hydrogen Peroxide → HCID 15290764, compound

HRID 258203Notes

Reaction equation

HRID 258203 reaction equation
[N:1]([CH:4]([CH:20]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH2:24][CH2:23][C:22]2[CH:31]=[CH:32][CH:33]=[CH:34][C:21]1=2)[C:5](N1C(C)C(C2C=CC=CC=2)OC1=O)=[O:6])=[N+:2]=[N-:3].[OH-:35].[Li+].OO.S([O-])([O-])=O.[Na+].[Na+]>O.O1CCCC1>[N:1]([C@H:4]([CH:20]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH2:24][CH2:23][C:22]2[CH:31]=[CH:32][CH:33]=[CH:34][C:21]1=2)[C:5]([OH:6])=[O:35])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 19782513HCID 19782513, compound

Product 1

HCID 15290764HCID 15290764, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of [4R-[3(R*),4α,5α]]-3 [azido(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)acetyl]-4-methyl5-phenyl-2-oxazolidinone (13.7 g, 30.27 mmol) in 4:1 tetrahydrofuran water (300 mL) at 0° C., is added a solution of lithium hydroxide (2.5 g, 60.54 mmol) in hydrogen peroxide (17.2 mL, 151.35 mmol, 30% aqueous) dropwise under nitrogen. The milky mixture is stirred at 0° C. for 1 hour. Aqueous sodium sulfite (50 mL) is added. The bulk o the tetrahydrofuran is evaporated in vacuo. The aqueous solution is cooled in an ice bath and acidified with 6N hydrochloric acid to pH 1. The white solid is extracted with dichloromethane (5X) and dried (magnesium sulfate). Evaporation of solvent in vacuo gives a yellow oil, which is purified by flash chromatography (silica gel, hexane ethyl acetate acetic acid/100:50:1) to yield the title compound as a white solid, 8.3 g; mp 101°-102° C., [α]D =-38.7° (c=1.0, methanol). The chiral auxiliary ((4R)-methyl-(5S) phenyl-2-oxazolidinone) is recovered as a white solid, 5.2 g; mp 120°-122° C.

Workup

  1. customThe bulk o the tetrahydrofuran is evaporated in vacuo
  2. temperatureThe aqueous solution is cooled in an ice bath
  3. extractionThe white solid is extracted with dichloromethane (5X)
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation of solvent in vacuo
  6. customgives a yellow oil, which
  7. customis purified by flash chromatography (silica gel, hexane ethyl acetate acetic acid/100:50:1)

Sources & evidence

ORD record
ord-e0bbfdf983544700926a220778917774
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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