Potassium Hydroxide → HCID 23680078, compound

HRID 2300259Notes

Reaction equation

HRID 2300259 reaction equation
[CH3:1][N:2]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:3]1[C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][N:6]=[C:5]2[O:14][N:15]=[C:16]([CH3:17])[C:4]=12.[OH-].[K+:35]>O1CCCC1CCO>[CH3:1][N:2]([S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:25][CH:26]=1)(=[O:20])=[O:19])[C:3]1[C:8]([C:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]2[O:14][N:15]=[C:16]([CH3:17])[C:4]=12.[K+:35]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18620563HCID 18620563, compound

Product 1

HCID 23680078HCID 23680078, compound

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

A mixture of 1.84 g (3.92 mmol) of the preceding ester and 4.71 ml of 1 N KOH in 10 ml of tetrahydrofuran-ethanol (1:1) was refluxed overnight and the solvent removed under vacuum. The residue was triturated with diethyl ether and filtered to give 1.59 g of potassium 4-{methyl-[4-(4-pyridinyloxy)benzene-sulfonyl]amino}-3-methylisoxazolo[5,4-b]pyridine-5-carboxylate as a pale yellow solid. Following the procedure of Example 91, the preceding potassium salt (1.45 g) was reacted with hydroxylamine to give a solid. The solid was partitioned between 30 ml of CH2Cl2 and 30 ml of H2O and filtered. The CH2Cl2 layer was stirred with 2 N citric acid (aqueous phase-pH 6). The solid which precipitated was filtered off and suspended in H2O. The aqueous suspension was adjusted to pH 7 with 1 N NaHCO3 and filtered. The solid was again suspended in H2O and the pH of the aqueous suspension adjusted to pH 6 with 2 N citric acid. The mixture was stirred and filtered to give 0.66 g of 4-{methyl-[4-(4-pyridinyl-oxy)benzenesulfonyl]amino}-3-methylisoxazolo[5,4-b]pyridine-5-carboxylic acid, hydroxyamide, m.p. 141° C. dec.

Workup

  1. temperaturewas refluxed overnight
  2. customthe solvent removed under vacuum
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-084a1b513b7f44608608b3dbbd98826c
Source dataset
uspto-grants-2002_12
Patent number
US06498167B2

Reaction notes

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