Triacetoxyperiodinane → (R)-5-Benzoyl-4'-methyl-N-(1-(6-methylpyridin-3-yl)ethyl)biphenyl-3-carboxamide

HRID 1845261Notes

Reaction equation

[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]1[CH:4]=[C:5]([C:16]([NH:18][C@@H:19]([C:21]2[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[CH3:20])=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:2]([C:3]1[CH:4]=[C:5]([C:16]([NH:18][C@@H:19]([C:21]2[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[CH3:20])=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1)(=[O:1])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-(hydroxy(phenyl)methyl)-4′-methyl-N—((R)-1-(6-methylpyridin-3-yl)ethyl)biphenyl-3-carboxamide (20 mg, 0.04 mmol) in methylene chloride (2.0 mL) was added Dess-Martin periodinane (26 mg, 0.061 mmol). The reaction mixture was stirred for 2 hours at 40° C., and LC-MS indicated the reaction was complete. The reaction solution was diluted with CH2Cl2, washed with 10% Na2S2O3, sat. aq. NaHSO3 and brine. The organic layer was dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel column to afford a white solid.

Workup

washwashed with 10% Na2S2O3, sat. aq. NaHSO3 and brine
dry with materialThe organic layer was dried over anhydrous MgSO4
concentrationconcentrated
customThe residue was purified by silica gel column
customto afford a white solid

Sources & evidence

ORD record: ord-618e9fd760ae4108b31dddbc776c4ad2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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