Potassium Carbonate → HCID 59485716, compound

HRID 1972267Notes

Reaction equation

CS([O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C@H:8]1[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=1)(=O)=O.[Cl:28][C:29]1[CH:30]=[CH:31][C:32](O)=[N:33][CH:34]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([N:9]2[C@@H:8]([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=3)[C@H:7]([CH2:6][O:5][C:32]3[CH:31]=[CH:30][C:29]([Cl:28])=[CH:34][N:33]=3)[O:11][C:10]2=[O:12])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 35 °C

Procedure

The ((4S,5R)-3-(4-chlorophenyl)-4-(3,5-difluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate (49 mg, 0.117 mmol), 5-chloropyridin-2-ol (45 mg, 0.35 mmol), and K2CO3 (48 mg, 0.35 mmol) are dissolved in DMF (1.0 mL) and stirred at 35° C. for 2 h, as judged complete by LC-MS. The reaction is diluted with water and ethyl acetate. The organic is washed with brine, dried over MgSO4, filtered and concentrated. Separation of the N- and O-alkylated products by preparative HPLC (C-18, 10-80% ACN/water (0.05% TFA)) gave 2.5 mg of the desired product. 1H NMR (acetone-d6, 400 MHz) δ 8.15 (d, 1H, J=2.7 Hz), 7.76 (dd, 1H, J=8.8, 2.7 Hz), 7.54-7.57 (m 2H), 7.32-7.36 (m, 2H), 7.22-7.28 (m, 2H), 7.02 (tt, 1H, J=9.1, 2.3 Hz), 6.86 (d, 1H, J=8.8 Hz), 5.77 (d, 1H, J=5.6 Hz), 4.85 (ddd, 1H, J=5.2, 4.0, 4.0 Hz), 4.72-4.79 (m, 2H). HPLC-MS calculated C21H14Cl2F2N2O3 (M+H+): 451.0, found: 451.0.

Workup

washThe organic is washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customSeparation of the N- and O-alkylated products by preparative HPLC (C-18, 10-80% ACN/water (0.05% TFA))

Sources & evidence

ORD record: ord-77ea05d4c8bf4505af5773107984f685
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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