Water → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid

HRID 1435851Notes

Reaction equation

HRID 1435851 reaction equation
[O:1]=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12]([O:14]C)=[O:13])=[N:11][C:4]=2[NH:3]1.O.[OH-].[Na+]>O1CCOCC1>[O:1]=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=[O:13])=[N:11][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21873660Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

Product 1

HCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acidYield 86.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (788 mg) in dioxane (120 ml)/water (30 ml) was treated dropwise over 2 hours with 0.5M NaOH solution (8 ml) and stirred overnight. After evaporation to approx. 3 ml, water (5 ml) was added and 2N HCl to pH=4. The precipitated solid was filtered off, washed with a small volume of water and dried under vacuum to give a solid (636 mg). MS (APCl−) m/e 209 ([M−H]−, 5%),165([M-COOH]−, 100%).

Workup

  1. customAfter evaporation to approx. 3 ml, water (5 ml)
  2. additionwas added
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with a small volume of water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-67de1d918c994e18aed99f2497ad7844
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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