Lithium Hydroxide → 2-(2-(5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)propanoic Acid

HRID 473286Notes

Reaction equation

HRID 473286 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:5]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH:30]3[CH2:32][CH2:31]3)=[CH:22][CH:21]=2)[C:6]([S:9][CH2:10][C:11]([NH:13][CH:14]([CH3:19])[C:15]([O:17]C)=[O:16])=[O:12])=[N:7][N:8]=1>C1COCC1.O>[Br:3][C:4]1[N:5]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH:30]3[CH2:32][CH2:31]3)=[CH:22][CH:21]=2)[C:6]([S:9][CH2:10][C:11]([NH:13][CH:14]([CH3:19])[C:15]([OH:17])=[O:16])=[O:12])=[N:7][N:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57811386Methyl 2-(2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)propanoate

Product 1

HCID 461789352-(2-(5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)propanoic Acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Aqueous lithium hydroxide solution (1M, 0.8 mL, 0.8 mmol) is added to a solution of methyl 2-(2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)propanoate (0.4 mmol) in 3:1, THF/H2O (1.6 mL) and the mixture stirred for 18 h at room temperature. The crude reaction mixture is concentrated and acidified with aqueous HCL (1M, 1.2 mL) and then is extracted with ethyl acetate (3×3 mL). The combined organic extracts are dried (sodium sulfate), filtered and concentrated to provide the desired product.

Workup

  1. customThe crude reaction mixture
  2. concentrationis concentrated
  3. extractionis extracted with ethyl acetate (3×3 mL)
  4. dry with materialThe combined organic extracts are dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b97b42d2e0ac499a816a600a0d210326
Source dataset
uspto-grants-2014_01
Patent number
US08633232B2

Reaction notes

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