HCID 86713171, compound → HCID 73603321, compound

HRID 1500284Notes

Reaction equation

[F:1][C:2]([F:33])([S:29]([CH3:32])(=[O:31])=[O:30])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[O:19]C(C)(C)[N:17]([C:22](=[O:26])[CH:23]([F:25])[F:24])[C@@H:16]3[CH2:27][F:28])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>Cl.O1CCOCC1.O>[F:33][C:2]([F:1])([S:29]([CH3:32])(=[O:30])=[O:31])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([OH:19])[C@H:16]([NH:17][C:22](=[O:26])[CH:23]([F:25])[F:24])[CH2:27][F:28])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 5 °C

Procedure

1-((4S,5R)-5-(4-(6-(difluoro(methylsulfonyl)methyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-3-yl)-2,2-difluoroethanone (30 mg, 0.06 mmol) is suspended in 4N hydrochloric acid in dioxane, cooled to 5° C. then treated with 2 drops of water, stirred 30 minutes then purified by HPLC to give the title compound (13 mg). 1H NMR (400 MHz, DMSO-d6) δ: 3.40 (s, 3H), 4.25-4.50 (m, 3H), 4.92 (m, 1H), 6.20 (t, J=56 Hz, 1H), 7.52 (d, J=8.2, 1H), 7.82 (d, J=8.2 Hz, 1H), 7.93 (d, J=8.2, 1H), 8.38 (dd, J=8.2 Hz and 2.1 Hz, 1H), 8.83 (d, J=8.6 Hz, 1H), 9.13 (d, J=1.8 Hz, 1H). m/z (Cl) 453 [M+H].

Workup

customthen purified by HPLC

Sources & evidence

ORD record: ord-d509af44c8fc4040bf4a6ad778412a26
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206126B2

Reaction notes

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