Hydrochloric Acid → (4-But-2-ynyloxy-benzenesulfonylamino)-acetic acid

HRID 2414548Notes

Reaction equation

HRID 2414548 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]#[C:19][CH3:20])=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.[OH-].[Na+].Cl>C1COCC1.CO>[CH2:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([S:7]([NH:6][CH2:5][C:4]([OH:21])=[O:3])(=[O:9])=[O:8])=[CH:15][CH:14]=1)[C:18]#[C:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54356225(4-But-2-ynyloxy-benzenesulfonylamino)-acetic acid ethyl ester

Product 1

HCID 22644772(4-But-2-ynyloxy-benzenesulfonylamino)-acetic acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 0.30 g (0.965 mmol) of the product of Example 20 in 10 mL of THF/methanol (1:1) was added 4.8 mL of a 1.0N sodium hydroxide solution and the reaction was stirred overnight at room temperature and then acidified to pH 2 with 10% HCl solution. The resulting mixture was extracted with dichloromethane and the combined organics were dried over MgSO4, filtered and concentrated in vacuo to provide 0.238 g (83%) of the sulfonamide as a white solid. Electrospray Mass Spec 281.9 (M−H)−

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane
  2. dry with materialthe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1d83d2a1fe24484bccd0d75ef7a2be4
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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