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

HRID 723928Notes

Reaction equation

HRID 723928 reaction equation
[NH3:1].[F:2][C:3]1[C:8]2[N:9]([CH3:13])[C:10](=[O:12])[O:11][C:7]=2[CH:6]=[C:5]([N:14]2[CH2:18][C@H:17]([C:19](OC)=[O:20])[O:16][C:15]2=[O:23])[CH:4]=1>CO>[F:2][C:3]1[C:8]2[N:9]([CH3:13])[C:10](=[O:12])[O:11][C:7]=2[CH:6]=[C:5]([N:14]2[CH2:18][C@H:17]([C:19]([NH2:1])=[O:20])[O:16][C:15]2=[O:23])[CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68489786methyl(5R)-3-(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Product 1

HCID 10214876(5R)-3-(4-Fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxamideYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ammonia 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-1,3-oxazolidine-5-carboxylate (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 (0.13 g, 55%); MS for C12H10FN3O5 m/z 296 (M+H)+; 1H NMR (DMSO-d6, 300 Mhz) δ 7.87 (br s, 1H), 7.63 (br s, 1H), 7.50 (d, 1H), 7.42 (dd, 1H), 5.03 (dd, 1H), 4.26 (t, 1H), 4.01 (dd, 1H), 3.42 (s, 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-59703f9b02804d04ae6ca3406ae4f6ce
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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