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

HRID 1991345Notes

Reaction equation

HRID 1991345 reaction equation
[CH2:1]([N:3]1[C:7]2[C:8]([F:22])=[CH:9][C:10]([N:12]3[CH2:16][C@H:15]([C:17]([O:19]C)=O)[O:14][C:13]3=[O:21])=[CH:11][C:6]=2[O:5][C:4]1=[O:23])[CH3:2].[NH3:24]>CO>[CH2:1]([N:3]1[C:7]2[C:8]([F:22])=[CH:9][C:10]([N:12]3[CH2:16][C@H:15]([C:17]([NH2:24])=[O:19])[O:14][C:13]3=[O:21])=[CH:11][C:6]=2[O:5][C:4]1=[O:23])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68490621methyl(5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Product 1

HCID 10236581(5R)-3-(3-Ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from methyl(5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate (Step 4, 0.250 g, 0.771 mmol) and ammonia in methanol (5 ml) according to the method of EXAMPLE 86, Step 10 (0.15 g, 63%); MS for C13H12FN3O5 m/z 310 (M+H)+; 1H NMR (DMSO-d6, 300 Mhz) δ 7.87 (br s, 1H), 7.63 (br s, 1H), 7.52 (d, 1H), 7.44 (dd, 1H), 5.03 (dd, 1H), 4.26 (t, 1H), 4.02 (dd, 1H), 3.86 (q, 2H), 1.28 (t, 3H).

Sources & evidence

ORD record
ord-bd335a8a83144e0aa7f9eeee231dc1c1
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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