Lithium Hydroxide → HCID 57617803, compound

HRID 2421848Notes

Reaction equation

HRID 2421848 reaction equation
[CH3:1][C:2]1([CH3:26])[S:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]([O:15]C)=[O:14])=[CH:12][C:6]=2[N:5]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:4][CH2:3]1.[OH-].[Li+]>C1COCC1.CO.O>[CH3:1][C:2]1([CH3:26])[S:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:6]=2[N:5]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67242533HCID 67242533, compound

Product 1

HCID 57617803HCID 57617803, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2,2-dimethyl-5-(phenylsulfonyl)-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine-7-carboxylate (450 mg, 1.149 mmol) in THF (10 mL), MeOH (10.00 mL) and water (10.00 mL) was added lithium hydroxide (55.1 mg, 2.299 mmol). The reaction was allowed to stir at room temperature for 8 h. The solvent was removed under reduced pressure. The aqueous solution was acidified with 1 N HCl (10 mL), which resulted in the formation of a white solid. The mixture was washed with EtOAc (3×30 mL) and the combined organics were dried over Na2SO4 and concentrated in vacuo. 2,2-dimethyl-5-(phenylsulfonyl)-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine-7-carboxylic acid (434 mg, 1.149 mmol, 100% yield) was isolated as an off white solid and used without further purification. LCMS (+ESI) m/z=377.9 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customresulted in the formation of a white solid
  3. washThe mixture was washed with EtOAc (3×30 mL)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9455c7b87dba4402b1f7131930869fb2
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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