tert-Butyl hydroperoxide → HCID 15042544, compound

HRID 249398Notes

Reaction equation

HRID 249398 reaction equation
C([O:5]O)(C)(C)C.[C:7]([O:11][C:12]([NH:14][C@H:15]([C@@H:23]([OH:27])[CH2:24][CH:25]=[CH2:26])[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([O:11][C:12]([NH:14][C@H:15]([C@@H:23]([OH:27])[C@@H:24]([OH:5])[CH:25]=[CH2:26])[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:13])([CH3:9])([CH3:8])[CH3:10]

Participants

3

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 10063230HCID 10063230, compound

Product 1

HCID 15042544HCID 15042544, compound

Procedure

An allylic oxidation using stoichiometric SeO2 and t-butyl hydroperoxide (Umbriet, M. A. and Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526) was performed on the resultant product of Example 50 to give the desired product after silica gel chromatography.

Sources & evidence

ORD record
ord-70603c225d2941909a8ff94874e1213e
Source dataset
uspto-grants-1993_05
Patent number
US05214129

Reaction notes

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