Ammonia → (5R)-3-(2,2-Difluoro-4-methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-7-yl)-2-oxo-5-oxazolidinecarboxamide

HRID 896185Notes

Reaction equation

HRID 896185 reaction equation
CO[C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:24]=[CH:23][C:14]3[N:15]([CH3:22])[C:16](=[O:21])[C:17]([F:20])([F:19])[O:18][C:13]=3[CH:12]=2)[CH2:6]1)=[O:4].[NH3:25]>CO>[F:20][C:17]1([F:19])[C:16](=[O:21])[N:15]([CH3:22])[C:14]2[CH:23]=[CH:24][C:11]([N:7]3[CH2:6][C@H:5]([C:3]([NH2:25])=[O:4])[O:9][C:8]3=[O:10])=[CH:12][C:13]=2[O:18]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68487729(5R)-3-(2,2-Difluoro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester

Product 1

HCID 10215199(5R)-3-(2,2-Difluoro-4-methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-7-yl)-2-oxo-5-oxazolidinecarboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of (5R)-3-(2,2-difluoro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester (Step 3, 50 mg, 0.14 mmol) in MeOH (1 mL) is added 2M NH3 in MeOH (2 mL, 4 mmol). The resulting mixture is stirred for 16 h at which time the reaction is concentrated under reduced pressure and purified by silica gel chromatography (EtOAc) to give the title compound as a light yellow solid (21 mg, 44%), 1H NMR (300 MHz, DMSO) δ 7.86 (br s, 1H), 7.61 (d, 2H), 7.52-7.41 (m, 2H), 5.02 (dd, 1H), 4.28 (t, 1H), 4.02 (dd, 1H), 3.42 (s, 3H); MS for C13H11F2N3O5 m/z 328.5 (M+H)+.

Workup

  1. concentrationis concentrated under reduced pressure
  2. custompurified by silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-1120c36c9053434395b5c28316cdb675
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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