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

HRID 1991352Notes

Reaction equation

HRID 1991352 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 (+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, 3H), 1.28 (t, 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-540950c3e36b4ad6b90c58df45de6920
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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