Methylamine → (5R)-3-(4-Fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-N-methyl-2-oxo-5-oxazolidinecarboxamide

HRID 723939Notes

Reaction equation

HRID 723939 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[C:9]2[N:10]([CH3:14])[C:11](=[O:13])[O:12][C:8]=2[CH:7]=[C:6]([N:15]2[CH2:19][C@H:18]([C:20]([O:22]C)=O)[O:17][C:16]2=[O:24])[CH:5]=1>CO>[F:3][C:4]1[C:9]2[N:10]([CH3:14])[C:11](=[O:13])[O:12][C:8]=2[CH:7]=[C:6]([N:15]2[CH2:19][C@H:18]([C:20]([NH:2][CH3:1])=[O:22])[O:17][C:16]2=[O:24])[CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68489786methyl(5R)-3-(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Product 1

HCID 10215011(5R)-3-(4-Fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-N-methyl-2-oxo-5-oxazolidinecarboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methylamine in methanol (2M, 5 ml) is added to solid methyl (5R)-3-(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 86, Step 9, 0.250 g, 0.806 mmol) and the suspension stirred overnight at room temperature. The reaction mixture is concentrated under reduced pressure and the residue purified by PTLC (10% methanol/dichloromethane) to give product as a white solid (0.049 g, 19%); MS for C13H12FN3O5 m/z 310 (M+H)+; 1H NMR (DMSO-d6, 300 Mhz) δ 8.40 (m, 1H), 7.49 (d, 1H), 7.42 (dd, 1H), 5.07 (dd, 1H), 4.26 (t, 1H), 4.02 (dd, 1H), 3.42 (s, 3H), 2.65 (d, 3H).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue purified by PTLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-fc74566136b14ff6b2086624f23044fc
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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