Hydrochloric Acid → HCID 46178767, compound

HRID 2061754Notes

Reaction equation

HRID 2061754 reaction equation
[OH-].[Li+].[NH2:3][C:4]1[N:5]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH:28]3[CH2:30][CH2:29]3)=[CH:20][CH:19]=2)[C:6]([S:9][C:10]([CH3:17])([CH3:16])[C:11]([O:13]CC)=[O:12])=[N:7][N:8]=1.Cl>C1COCC1.CO>[NH2:3][C:4]1[N:5]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH:28]3[CH2:30][CH2:29]3)=[CH:20][CH:19]=2)[C:6]([S:9][C:10]([CH3:17])([CH3:16])[C:11]([OH:13])=[O:12])=[N:7][N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57811380HCID 57811380, compound

Product 1

HCID 46178767HCID 46178767, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide solution (1M aqueous, 0.757 mL, 0.757 mmol) was added to a solution of ethyl 2-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate (100 mg, 0.252 mmol) in THF (2 mL) and methanol (1 mL) and the mixture stirred at room temperature for 20 h. The crude reaction mixture was acidified with HCl (1N, 1 mL) and sonicated to break up the solids, which were then isolated by filtration to give 2-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoic acid as a white solid (69 mg, 74%).

Workup

  1. customThe crude reaction mixture
  2. customsonicated
  3. customwere then isolated by filtration

Sources & evidence

ORD record
ord-6d4952f9559c4431adf30306b69b9125
Source dataset
uspto-grants-2012_10
Patent number
US08283369B2

Reaction notes

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