Sodium Hydroxide → Lesinurad Sodium

HRID 38744Notes

Reaction equation

[OH-].[Na+:2].[Br:3][C:4]1[N:5]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]3[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)[C:6]([S:9][CH2:10][C:11]([OH:13])=[O:12])=[N:7][N:8]=1>C(O)C>[Br:3][C:4]1[N:5]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]3[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)[C:6]([S:9][CH2:10][C:11]([O-:13])=[O:12])=[N:7][N:8]=1.[Na+:2]

Participants

Conditions

Temperature: 10 °C

Procedure

Aqueous sodium hydroxide solution (1M, 2.0 mL, 2.0 mmol) was added dropwise over 5 min to a solution of 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (810 mg, 2.0 mmol) in ethanol (10 mL) at 10° C. The mixture was stirred at 10° C. for a further 10 min. Volatile solvents were removed in vacuo to dryness to provide sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate as a solid (850 mg, 100%).

Workup

customVolatile solvents were removed in vacuo to dryness

Sources & evidence

ORD record: ord-86a2ae5f77cf4d70be41e8543aab5a70
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524754B2

Reaction notes

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