Hydrogen Peroxide → 2-[2-(Tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid

HRID 479609Notes

Reaction equation

HRID 479609 reaction equation
C([C@H]1COC(=O)N1[C:14]([CH:16]([CH2:25][CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])C1C=CC=CC=1.[OH:34]O.O.[OH-].[Li+]>O1CCCC1.O>[C:21]([O:20][C:18](=[O:19])[CH2:17][CH:16]([CH2:25][CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:14]([OH:15])=[O:34])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 69430893tert-Butyl 3-{[(4S)-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-6-cyclohexylhexanoate

Product 1

HCID 213050372-[2-(Tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidYield 97.5%

Reagents, catalysts & solvents 1

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

Procedure

A solution of tert-butyl 3-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-6-cyclohexylhexanoate (64.0 g, 139.9 mmol) in tetrahydrofuran:water (3:1, 800 ml) was cooled to 5° C. then treated sequentially with hydrogen peroxide (30%w/v water, 87 ml, 769 mmol) then lithium hydroxide hydrate (10.0 g, 238 mmol). The reaction was stirred for 1 hour then quenched by dropwise addition of an aqueous solution of sodium thiosulphate (500 ml) keeping the temperature below 20° C. The mixture was extracted with ethyl acetate (discarded) and the aqueous phase was acidifed to pH 2 with solid citric acid and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of hexane: ethyl acetate (2:1) gradually changing to hexane: ethyl acetate (1:1) to afford the title compound (40.7 g)

Workup

  1. customthen quenched by dropwise addition of an aqueous solution of sodium thiosulphate (500 ml)
  2. customthe temperature below 20° C
  3. extractionThe mixture was extracted with ethyl acetate (discarded)
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of hexane: ethyl acetate (2:1)

Sources & evidence

ORD record
ord-ecbf213057114aa1a1e978b68f943b53
Source dataset
uspto-grants-2003_11
Patent number
US06645993B2

Reaction notes

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