Lithium Hydroxide → HCID 57811449, compound

HRID 1921728Notes

Reaction equation

HRID 1921728 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][CH2:14][C:15]([O:17]CC)=[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][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[N:7][N:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66985365HCID 66985365, compound

Product 1

HCID 57811449HCID 57811449, compound

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 ethyl 2-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)acetate (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 2-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)acetic acid.

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-0d02c21eab824549b709ea11a90aa49e
Source dataset
uspto-grants-2012_05
Patent number
US08173690B2

Reaction notes

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