Lithium hydroxide, monohydrate → HCID 9935937, compound

HRID 1386030Notes

Reaction equation

HRID 1386030 reaction equation
C[O:2][C:3]([C:5]1[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[S:7](=[O:26])(=[O:25])[C:8]2[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=2[C:10]=1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:4].O.[OH-].[Li+]>CO.O>[CH3:18][O:17][C:15]1[CH:16]=[C:11]([C:10]2[C:9]3[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=3[S:7](=[O:26])(=[O:25])[N:6]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:34])[F:35])[C:5]=2[C:3]([OH:4])=[O:2])[CH:12]=[C:13]([O:19][CH3:20])[CH:14]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15512895HCID 15512895, compound

Product 1

HCID 9935937HCID 9935937, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The solution of 4-(3,5-dimethoxy-phenyl)-2-(2-trifluoromethyl-phenyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester (1.29 g, 2.5 mmol) and lithium hydroxide monohydrate (0.3 g 12.5 mmol) in 30 mL of MeOH and 15 mL water was refluxed for 2.5 hours and evaporated to an oil. The residue was dissolved in water, washed with ethyl ether, and the aqueous layer decanted. The aqueous layer was acidified to pH 1 with concentrated HCl and extracted into ethyl ether, washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to a foam. The residue was chromatographed on 50 g silica gel eluted with chloroform, and the appropriate fractions were concentrated in vacuo and evaporated from ethyl ether giving a solid foam. 1.4 g, 66% yield. NMR spectra and elemental analysis were consistent with the structure.

Workup

  1. customevaporated to an oil
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl ether
  4. customthe aqueous layer decanted
  5. extractionextracted into ethyl ether
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to a foam
  10. customThe residue was chromatographed on 50 g silica gel
  11. washeluted with chloroform
  12. concentrationthe appropriate fractions were concentrated in vacuo
  13. customevaporated from ethyl ether giving a solid foam

Sources & evidence

ORD record
ord-cc18792161e04fcdbff6fcaabe5c808f
Source dataset
uspto-grants-2001_07
Patent number
US06265399B1

Reaction notes

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