Lithium Hydroxide → HCID 57811337, compound

HRID 1921712Notes

Reaction equation

HRID 1921712 reaction equation
[OH-].[Li+].[CH:3]1([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([N:16]3[C:20]([C:21]([F:24])([F:23])[F:22])=[N:19][N:18]=[C:17]3[S:25][C:26]([CH3:33])([CH3:32])[C:27]([O:29]CC)=[O:28])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1>C1COCC1>[CH:3]1([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([N:16]3[C:20]([C:21]([F:22])([F:24])[F:23])=[N:19][N:18]=[C:17]3[S:25][C:26]([CH3:33])([CH3:32])[C:27]([OH:29])=[O:28])=[CH:8][CH:7]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58491079HCID 58491079, compound

Product 1

HCID 57811337HCID 57811337, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide solution (1M aqueous, 0.67 mL, 0.67 mmol) was added to a solution of ethyl 2-(4-(4-cyclopropylnaphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate (0.1 g, 0.22 mmol) in THF (0.88 mL) and the mixture stirred at room temperature for 18 h. The crude reaction mixture was concentrated; water (100 mL) added and then washed with ethyl acetate (2×40 mL). The aqueous layer was acidified with HCl (1N aqueous, 10 mL) and extracted with ethyl acetate (30 mL). The combined organic extracts were dried over sodium sulfate and concentrated to afford 2-(4-(4-cyclopropylnaphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoic acid as an off-white solid (49 mg, 53%).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. additionwater (100 mL) added
  4. washwashed with ethyl acetate (2×40 mL)
  5. extractionextracted with ethyl acetate (30 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ce7b7459f2247f680fac1b4b5871bc5
Source dataset
uspto-grants-2012_05
Patent number
US08173690B2

Reaction notes

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