Hydrogen Peroxide → HCID 69007375, compound

HRID 1985391Notes

Reaction equation

HRID 1985391 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C@H:16]([O:32][CH:33]([CH3:35])[CH3:34])[C:17](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH:37]O.[OH-].[Li+].O>O1CCCC1>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[CH:10]=[C:11]([CH2:15][C@H:16]([O:32][CH:33]([CH3:35])[CH3:34])[C:17]([OH:18])=[O:37])[CH:12]=[CH:13][CH:14]=1)=[O:36])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3939Lithium HydroxideHCID 57719462HCID 57719462, compound

Product 1

HCID 69007375HCID 69007375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.3 g of {3-[3-(4 (S)-Benzyl-2-oxooxazolidin-3-yl)-2(S)-isopropoxy-3-oxopropyl]benzyl}carbamic acid t-butyl ester was dissolved in 300 ml of tetrahydrofuran, and 15 ml of 30% aqueous hydrogen peroxide and 75 ml of 1N aqueous lithium hydroxide were successively added under ice-cooling, and stirring was continued overnight at room temperature. The reaction solution was treated with water, extracted with dichloromethane, and the aqueous layer was acidified with 1N hydrochloric acid. The mixture was extracted (×3) with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 16.68 g of 3-[3-(t-butoxycarbonylaminomethyl)phenyl]-2(S)-isopropoxypropionic acid. The product was then dissolved in 100 ml of N,N-dimethylformamide, and 7 g of potassium hydrogen carbonate and 3.5 ml of iodomethane were successively added, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 8.58 g of the title compound as a white solid in the 4:1 hexane-ethyl acetate fraction.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. extractionThe mixture was extracted (×3) with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f44224a5cd74c438bb53419934841f9
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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