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

HRID 734215Notes

Reaction equation

HRID 734215 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 h with 0.5M NaOH solution (8 mL) and stirred overnight. After evaporation to approx. 3 ml, water (5 mL) was added and 2M HCl to pH4. The precipitated solid was filtered off, washed with a small volume of water and dried under vacuum to give a solid (636 mg); LC/MS (APCI−) m/z 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-e7e75db7cd6a460dbb99c4f2e3a3cfaf
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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