Hydrogen Peroxide → HCID 11805344, compound

HRID 1944786Notes

Reaction equation

HRID 1944786 reaction equation
OO.C([C@H]1COC(=O)N1[C:16](=[O:27])[C@@H:17]([CH2:25][OH:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C1C=CC=CC=1.O.[OH-].[Li+].S([O-])([O-])=[O:32].[Na+].[Na+]>O.C1COCC1>[OH:26][CH2:25][C@@H:17]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:16]([OH:27])=[O:32]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 54268323HCID 54268323, compound

Product 1

HCID 11805344HCID 11805344, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

9 M of Hydrogen peroxide in water (50 mL) was added to a solution of intermediate (7c) (14.8 g, 43.6 mmol) in THF (100 mL) at 0° C. followed by the addition of aqueous 1.5 M lithium hydroxide monohydrate (58 mL). After 2.5 hours at room temperature, sodium sulfite (10 g) in water (100 mL) was added and the mixture was stirred for 30 minutes. The mixture was extracted with water (300 mL) and chloroform (2×150 mL). The aqueous layer was acidified to pH2 with aqueous 6M HCl and extracted with EtOAc (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield intermediate (7d), which was used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted with water (300 mL) and chloroform (2×150 mL)
  2. extractionextracted with EtOAc (3×200 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e3fa5acbd734a0d8f04bbe309a257a3
Source dataset
uspto-grants-2013_03
Patent number
US08394846B2

Reaction notes

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