Triacetoxyperiodinane → HCID 23286243, compound

Reaction equation

CC(OI1(O[C:20]([CH3:22])=[O:21])(OC(C)=O)OC(=O)[C:11]2[CH:10]=C[CH:8]=[CH:7][C:6]1=2)=O.[C:23](OCC)(=O)C.ClCCl>>[CH3:23][C:20]([CH3:22])=[O:21].[CH3:10][CH2:11][CH2:6][CH2:7][CH3:8]

Participants

Reactant 2

HCID 159087Triacetoxyperiodinane

HCID 21226138Dichloromethane ethylacetate

Product 1

HCID 23286243HCID 23286243, compoundYield 46%

Procedure

The title derivative was prepared from the compound of Example 11, Step A, using the Dess-Martin oxidation method given in Example 2, Step C (but with a larger excess of periodinane). It was purified by flash chromatography (silica gel, ethyl acetate/dichloromethane: 2/8, Rf: 0.35) and crystallization from acetone/pentane (46% yield). Analysis calculated for C38H38N4O8N2 : C, 63.38; H, 5.54; N, 7.82. Found: C, 63.49; H, 5.33; N, 7.75.

Sources & evidence

ORD record: ord-b44c952b2fcb4f0089943dfe4ff0f693
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716973

Reaction notes

Loading…