tert-Butyl hydroperoxide → HCID 15042544, compound

HRID 1086862Notes

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

Reactant 2

HCID 6410tert-Butyl hydroperoxide

HCID 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-ceaf228728a043c8acf02e96c6016abf
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05032577

Reaction notes

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