Lithium Hydroxide → HCID 57617823, compound

HRID 2421842Notes

Reaction equation

HRID 2421842 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]3[CH:17]=[CH:18][C:19]([C:21]([O:23]C)=[O:22])=[CH:20][C:12]2=3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]3[CH:17]=[CH:18][C:19]([C:21]([OH:23])=[O:22])=[CH:20][C:12]2=3)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67241383HCID 67241383, compound

Product 1

HCID 57617823HCID 57617823, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-fluorophenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate (1.779 g, 4.84 mmol) in THF (12 mL) and water (6 mL) was added LiOH (0.6096 g). The reaction was allowed to stir at room temperature for 16 hours. LCMS analysis identified the product as the predominant component of the reaction mixture. The solvent was removed under reduced pressure. The resulting aqueous solution was acidified with 1N HCl to provide a white precipitate. The aqueous layer was extracted with DCM until the acid was no longer detected in the organic wash layer. The combined organics were washed with H2O and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The mixture was purified by flash chromatography using a gradient elution of hexane with 0-95% ethyl acetate doped with 1% AcOH. The product, 4-(4-fluorophenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylic acid (1.108 g, 3.14 mmol, 65% yield), was isolated as off-white solid. LCMS (+ESI) m/z=354.0 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto provide a white precipitate
  3. extractionThe aqueous layer was extracted with DCM until the acid
  4. washThe combined organics were washed with H2O
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe mixture was purified by flash chromatography
  9. washa gradient elution of hexane with 0-95% ethyl acetate

Sources & evidence

ORD record
ord-c3d105411da0419abdaf0d1bbf774fd7
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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