Hydrogen Peroxide → HCID 16125606, compound

HRID 1987467Notes

Reaction equation

[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][CH2:15][C:16]([OH:33])([CH3:32])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:39].[OH2:49]>ClCCl.[Cl-].[Na+].O>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([CH2:15][C:16]([OH:33])([CH3:32])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:21]=1)=[O:18])(=[O:39])=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

3-(2-benzylphenylthio)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (32 mg, 0.068 mmol) was dissolved in dichloromethane (0.1 mL) and cooled to −78° C. 30% hydrogen peroxide (12 μL, 0.4 mmol) was added followed by the slow addition of trifluoroacetic anhydride (48 μL, 0.34 mmol). The reaction was stirred at room temperature for 16 h. The reaction was diluted with dichloromethane. Cold water and brine were added, and the reaction was stirred for 20 minutes. The organic layer was separated, dried over magnesium sulfate, filtered and evaporated. Purification by column chromatography (hexane:EtOAc 50:50) yielded 14 mg of desired product. Production of PLM2 was confirmed by 13-C NMR and mass spectral analysis.

Workup

stirringthe reaction was stirred for 20 minutes
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customPurification by column chromatography (hexane:EtOAc 50:50)

Sources & evidence

ORD record: ord-1c013845c3024d388a9648e56ce9455b
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550505B2

Reaction notes

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