Ammonia → HCID 10308770, compound

HRID 896159Notes

Reaction equation

HRID 896159 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-c361645ab8b4491ba662d5458bc44116
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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