p-Toluenesulfonic acid → HCID 69002385, compound

HRID 2105532Notes

Reaction equation

HRID 2105532 reaction equation
[OH:1][CH:2]([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:3]([OH:5])=[O:4].[CH3:17][C:18]1C=CC(S(O)(=O)=O)=C[CH:23]=1>COC(OC)(C)C>[CH3:17][C:18]1([CH3:23])[O:1][CH:2]([CH:6]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7]2)[C:3](=[O:5])[O:4]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69004806HCID 69004806, compound

Product 1

HCID 69002385HCID 69002385, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A mixture of hydroxy-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid (0.13 mmol) and p-TSA (1 mg) in 1.5 mL of 2,2-dimethoxypropane is stirred at room temperature for 16 hours. Solvent is removed under vacuum and the residue is treated with a saturated aqueous solution of NaHCO3 (2 mL). The resulted mixture is extracted with EtOAc (3×5 mL). The organic layers are combined and concentrated to provide the crude 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-4H-benzo[1,4]thiazin-3-one which was used directly for next step without further purification. Yield: 31%

Workup

  1. customSolvent is removed under vacuum
  2. additionthe residue is treated with a saturated aqueous solution of NaHCO3 (2 mL)
  3. extractionThe resulted mixture is extracted with EtOAc (3×5 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-542139e5783b4529913f817734eb3574
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

Loading…