Acetonitrile → HCID 118021407, compound

HRID 531275Notes

Reaction equation

[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[F:9][C:10]([F:53])([F:52])[C:11]1[CH:12]=[C:13]([C@H:21]2[O:25][C:24](=[O:26])[N:23]([CH2:27][C:28]3[C:33]([C:34]4[C:35]([O:47][CH3:48])=[N:36][CH:37]=[C:38]([C:40]([OH:46])([CH3:45])[C:41]([F:44])([F:43])[F:42])[CH:39]=4)=[CH:32][N:31]=[C:30](SC)[N:29]=3)[C@H:22]2[CH3:51])[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.[C:54](#N)C>O.C(OC)(C)(C)C>[F:20][C:17]([F:18])([F:19])[C:15]1[CH:14]=[C:13]([C@H:21]2[O:25][C:24](=[O:26])[N:23]([CH2:27][C:28]3[C:33]([C:34]4[C:35]([O:47][CH3:48])=[N:36][CH:37]=[C:38]([C:40]([OH:46])([CH3:45])[C:41]([F:44])([F:43])[F:42])[CH:39]=4)=[CH:32][N:31]=[C:30]([S:1]([CH3:54])(=[O:6])=[O:2])[N:29]=3)[C@H:22]2[CH3:51])[CH:12]=[C:11]([C:10]([F:53])([F:52])[F:9])[CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium peroxymonosulfate (528 mg, 0.859 mmol) was added (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-{2-methoxy-5-[(2RS)-1,1,1-trifluoro-2-hydroxypropan-2-yl]pyridin-3-yl}-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (Step A, 240 mg, 0.358 mmol) in acetonitrile (2 mL) and water (1 mL) and stirred for 1 hour at 60° C. (bath was turned off immediately and allowed to cool to 25° C. over 1 hour); LCMS showed complete conversion to product. The reaction was diluted with 20 mL methyl t-butyl ether and poured into 20 mL water; the organic layer was washed twice with water (20 mL) and finally with 50 mL brine, dried over sodium sulfate and concentrated to afford white solid.

Workup

temperatureto cool to 25° C. over 1 hour)
washthe organic layer was washed twice with water (20 mL) and finally with 50 mL brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customto afford white solid

Sources & evidence

ORD record: ord-e0c4fe9116dc4ef483bbfebd5d84f2cd
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353101B2

Reaction notes

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