Ammonia → HCID 10308770, compound

HRID 723883Notes

Reaction equation

HRID 723883 reaction equation
C([O:5][C:6]([C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][CH2:22][C:23](=[O:26])[NH:24][N:25]=3)=[C:16]([F:27])[CH:15]=2)[CH2:9]1)=O)CCC.[NH3:28]>CO>[F:27][C:16]1[CH:15]=[C:14]([N:10]2[CH2:9][C@H:8]([C:6]([NH2:28])=[O:5])[O:12][C:11]2=[O:13])[CH:19]=[CH:18][C:17]=1[C:20]1[S:21][CH2:22][C:23](=[O:26])[NH:24][N:25]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68488930HCID 68488930, compound

Product 1

HCID 10308770HCID 10308770, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[3-Fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid butyl ester (Step 6, 0.300 g, 0.758 mmol) is dissolved in 2M ammonia in methanol solution (8 ml) and stirred overnight at room temperature. The reaction is concentrated under vacuum and purified by PTLC (10% methanol/CH2Cl2) to give the title compound as a white solid (0.22 g, 87%), mp 249–251° C.; 1H NMR (300 Mhz, CDCl3) δ 3.59 (s, 2H), 4.04 (dd, 1H), 4.30 (t, 1H), 5.05 (dd, 1H), 7.49–7.72 (m, 4H), 7.88 (br s, 1H), 11.63 (s, 1H); MS (m/z) for C13H11FN4O4S: [M+H]+=339.

Workup

  1. concentrationThe reaction is concentrated under vacuum
  2. custompurified by PTLC (10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-d7596b836068404a8fde657f034dd293
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

Loading…