Hydrogen Peroxide → HCID 87901224, compound

HRID 1796859Notes

Reaction equation

HRID 1796859 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:24])[C@@H:15]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][CH:17]=[CH2:18])C1C=CC=CC=1.[OH:25]O.O.[OH-].[Li+]>C1COCC1.O>[CH3:23][CH:21]([CH3:22])[CH2:20][CH2:19][C@@H:15]([CH2:16][CH:17]=[CH2:18])[C:14]([OH:24])=[O:25]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 69589206HCID 69589206, compound

Product 1

HCID 87901224HCID 87901224, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of Example 8C (17.3 g, 52.6 mmol) in THF (200 mL) was added water (25 mL) and 30% hydrogen peroxide (25 mL, 220 mmol). A solution of lithium hydroxide monohydrate (4.38 g, 104 mmol) in water (100 mL) was added and the resulting solution was stirred for 12 hours. The mixture was quenched with aqueous NaHSO3 then concentrated and made basic with 5M NaOH. The aqueous phase was washed with ethyl acetate, then acidified with concentrated HCl to pH 3 and extracted twice with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 171 (M+H)+.

Workup

  1. customThe mixture was quenched with aqueous NaHSO3
  2. concentrationthen concentrated
  3. washThe aqueous phase was washed with ethyl acetate
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4f44daac2c5a45e3ad5e4192db4eb443
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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