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

HRID 896216Notes

Reaction equation

HRID 896216 reaction equation
[CH3:1][NH2:2].[CH2:3]([N:5]1[C:9]2[C:10]([F:24])=[CH:11][C:12]([N:14]3[CH2:18][C@H:17]([C:19]([O:21]C)=O)[O:16][C:15]3=[O:23])=[CH:13][C:8]=2[O:7][C:6]1=[O:25])[CH3:4]>CO>[CH2:3]([N:5]1[C:9]2[C:10]([F:24])=[CH:11][C:12]([N:14]3[CH2:18][C@H:17]([C:19]([NH:2][CH3:1])=[O:21])[O:16][C:15]3=[O:23])=[CH:13][C:8]=2[O:7][C:6]1=[O:25])[CH3:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68490621methyl(5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Product 1

HCID 10125745(5R)-3-(3-Ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-N-methyl-2-oxo-5-oxazolidinecarboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methylamine in methanol (2M, 5 ml) is added to solid methyl (5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 87, Step 4, 0.250 g, 0.771 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 (0.10 g, 40%); MS for C14H14FN3O5 m/z 324 (M+H)+; 1H NMR (DMSO-d6, 300 Mhz) δ 8.40 (m, 1H), 7.51 (d, 1H), 7.44 (dd, 1H), 5.07 (dd, 1H), 4.27 (t, 1H), 4.02 (dd, 1H), 3.85 (q, 2H), 2.65 (d, 31H), 1.28 (t, 31H).

Workup

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

Sources & evidence

ORD record
ord-b66e202bf5b44af2bcaa9dc3f55e0c25
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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