Hydrogen Peroxide → HCID 16125605, compound

HRID 1158188Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[C:11]([OH:25])([CH3:24])[CH2:12][S:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:27]([F:30])([F:29])[F:28])#[N:2].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:36].[OH2:46]>ClCCl.[Cl-].[Na+].O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[C:11]([OH:25])([CH3:24])[CH2:12][S:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)(=[O:36])=[O:46])=[CH:5][C:4]=1[C:27]([F:29])([F:28])[F:30])#[N:2]

Participants

Conditions

Temperature: -78 °C

Procedure

N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(naphthalen-1-ylthio)propanamide (31 mg, 0.072 mmol) was dissolved in dichloromethane (0.2 mL) and cooled to −78° C. 30% hydrogen peroxide (16.7 μL, 0.58 mmol) was added followed by the slow addition of trifluoroacetic anhydride (62 μL, 0.43 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 25 mg of desired product. Production of PLM1 was confirmed by 1-H NMR, 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-457465ac03024dcdb644c5eb0446a5bc
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807713B2

Reaction notes

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