Water → HCID 69004806, compound

HRID 851916Notes

Reaction equation

HRID 851916 reaction equation
C([O:3][C:4](=[O:18])[CH:5]([OH:17])[CH:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7]1)C.[OH-].[Na+].O>CCO>[OH:17][CH:5]([CH:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7]1)[C:4]([OH:18])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69004783HCID 69004783, compound

Product 1

HCID 69004806HCID 69004806, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of hydroxy-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid ethyl ester (1.12 mmol) in 5 mL of EtOH is added NaOH (1N) (2.24 mmol) and the mixture is stirred at room temperature for 1 hour. Water (20 ml) is added into the mixture followed by extraction (EtOAc, 3×10 mL). The aqueous layer is then treated with HCl (1N) (2.5 mL) and extracted with EtOAc (3×30 mL). The combined extracts are washed with brine and dried over MgSO4. After filtering off the drying agent, the solution is concentrated to provide the crude product hydroxy-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid as a off white solid. Yield: 76%. MS: (ES+): 240 [M+1].

Workup

  1. extractionfollowed by extraction (EtOAc, 3×10 mL)
  2. additionThe aqueous layer is then treated with HCl (1N) (2.5 mL)
  3. extractionextracted with EtOAc (3×30 mL)
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtering off the drying agent
  7. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-00ad125ca5f94b9eb890f2ee4bcd0515
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

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