Hydrogen Peroxide → HCID 54500721, compound

HRID 130545Notes

Reaction equation

HRID 130545 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][C@@H:8]([C:16](N1[C@H](C)[C@H](C2C=CC=CC=2)OC1=O)=[O:17])[CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[OH:32]O>C1COCC1.O>[C:1]([O:5][C:6](=[O:31])[CH2:7][C@H:8]([CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])[C:16]([OH:17])=[O:32])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 57052159(3S,5R)-5-Methyl-3-((4R,5S)-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-nonanoic acid tert-butyl ester

Product 1

HCID 54500721HCID 54500721, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester 138 (2.65 g, 6.14 mmol) in 20 mL THF at 0° C. was added a precooled (0° C.) solution of LiOH monohydrate (1.0 g, 23.8 mmol) and hydrogen peroxide (30 wt % aqueous soln, 5.0 mL) in 10 mL H2O. The mixture was stirred vigorously for 90 minutes, then warmed to ambient temperature and stirred 90 minutes. The reaction was quenched at 0° C. by addition of 100 mL 10% NaHSO3 (aq), then extracted with Et2O. The phases were separated, and the organic phase washed with brine, dried (MgSO4), and concentrated. The crude acid 139 was used without purification.

Workup

  1. stirringstirred 90 minutes
  2. customThe reaction was quenched at 0° C. by addition of 100 mL 10% NaHSO3 (aq)
  3. extractionextracted with Et2O
  4. customThe phases were separated
  5. washthe organic phase washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude acid 139 was used without purification

Sources & evidence

ORD record
ord-3f7ab3f05ec54a33ab44f2861f858360
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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