Sodium Hydroxide → HCID 22907071, compound

HRID 264304Notes

Reaction equation

HRID 264304 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]2([C:19]([O:21]C)=[O:20])[CH2:18][CH2:17][S:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]2([C:19]([OH:21])=[O:20])[CH2:14][CH2:15][S:16][CH2:17][CH2:18]2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 22907197HCID 22907197, compound

Product 1

HCID 22907071HCID 22907071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-carbomethoxy-tetrahydrothiopyran (800.0 mg, 1.9 mmol) in methanol (50 mL) is added 1N sodium hydroxide (25 mL). The mixture is heated to reflux for 10 hours, and then solid sodium hydroxide is added (3.0 g, excess) and refluxing is continued for 18 hours. The mixture is concentrated to a volume of approximately 30 mL and acidified with citric acid (pH=5). The mixture is partitioned between ethyl acetate and water. The organic layer is removed, washed with brine, dried (MgSO4), and the solvent is evaporated to give 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-carboxytetrahydrothiopyran.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 10 hours
  3. temperaturerefluxing
  4. concentrationThe mixture is concentrated to a volume of approximately 30 mL
  5. customThe mixture is partitioned between ethyl acetate and water
  6. customThe organic layer is removed
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent is evaporated

Sources & evidence

ORD record
ord-5b8dc8d82d414b14979dc8b89793ec19
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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