Lithium Hydroxide → 1-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylic acid

HRID 885586Notes

Reaction equation

HRID 885586 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:5]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH:29]3[CH2:31][CH2:30]3)=[CH:21][CH:20]=2)[C:6]([S:9][C:10]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12][CH2:11]2)=[N:7][N:8]=1>C1COCC1.CO>[Br:3][C:4]1[N:5]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH:29]3[CH2:31][CH2:30]3)=[CH:21][CH:20]=2)[C:6]([S:9][C:10]2([C:14]([OH:16])=[O:15])[CH2:11][CH2:12][CH2:13]2)=[N:7][N:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57811367ethyl 1-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylate

Product 1

HCID 578114151-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Lithium hydroxide solution (1M aqueous, 0.387 mL, 0.387 mmol, 3 eq) was added to a solution of ethyl 1-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylate (61 mg, 0.129 mmol) in THF/methanol (2/1, 3 mL) and the mixture stirred at room temperature for 18 h. The mixture was acidified with HCL (1N aqueous, 0.645 mL, 0.645 mmol, 5 eq), concentrated, water (10 mL) added and extracted with diethyl ether (2×15 mL). The combined organic extracts were dried over calcium chloride and concentrated to give 1-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)cyclobutanecarboxylic acid as an off-white solid (43 mg, 75%).

Workup

  1. concentrationconcentrated
  2. additionwater (10 mL) added
  3. extractionextracted with diethyl ether (2×15 mL)
  4. dry with materialThe combined organic extracts were dried over calcium chloride
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f8e150286254845ab030b44114b79f5
Source dataset
uspto-grants-2012_08
Patent number
US08242154B2

Reaction notes

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