Ammonia → HCID 60018004, compound

HRID 896180Notes

Reaction equation

C([O:5][C:6]([C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([N:21]3[CH:26]=[CH:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[C:16]([F:28])[CH:15]=2)[CH2:9]1)=O)CCC.CO.[NH3:31]>>[O:27]=[C:24]1[CH:25]=[CH:26][N:21]([C:17]2[C:16]([F:28])=[CH:15][C:14]([N:10]3[CH2:9][C@H:8]([C:6]([NH2:31])=[O:5])[O:12][C:11]3=[O:13])=[CH:19][C:18]=2[F:20])[CH2:22][CH2:23]1

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 68486037HCID 68486037, compound

Product 1

HCID 60018004HCID 60018004, compound

Procedure

(5R)-3-[3,5-Difluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid butyl ester (Step 5, 200 mg, 0.50 mmol) is dissolved in a 2M solution of NH3 in MeOH (4 mL, 8 mmol). The resulting solution is stirred at room temperature for 3 h at which time the reaction mixture is concentrated under reduced pressure. The residue is washed with ether to give the title compound as an off white solid (139 mg, 82%), 1H NMR (300 MHz, DMSO) δ 7.89 (br s, 1H), 7.64 (br s, 1H), 7.54-7.38 (m, 3H), 5.07-4.98 (m, 2H), 4.26 (t, 1H), 4.01 (dd, 1H), 3.78 (t, 2H); MS for C15H13F2N3O4 m/z 338.4 (M+H)+.

Workup

concentrationis concentrated under reduced pressure
washThe residue is washed with ether

Sources & evidence

ORD record: ord-a397a6174cfb4fee88afb32aa457e584
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919329B2

Reaction notes

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