Lithium hydroxide, monohydrate → 3-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide

HRID 517717Notes

Reaction equation

C([O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]#[N:22])[CH:12]=2)[N:9]=[N:8][N:7]=1)(=O)C.[OH2:23].[OH-].[Li+]>CO.O1CCCC1.O>[OH:4][CH2:5][C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:21]([NH2:22])=[O:23])[N:9]=[N:8][N:7]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

A solution of {1-[3-cyano-5-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 30, 3.33 g) in methanol (10.0 mL), tetrahydrofuran (20 mL) and water (10.0 mL) was cooled in an ice-water bath before the addition of lithium hydroxide monohydrate (0.449 g, 10.7 mmol). The reaction was stirred at 0-5° C. for 2 hours. The reaction was diluted with water (30 mL) and the organic solvent removed under vacuum. The suspension was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried and the solvent removed to yield a white solid. The solid was triturated with diethyl ether (2×25 mL), the solvent decanted and the residue dried under vacuum to yield the intermediate 3-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide as a white solid (1.37 g).

Workup

customthe organic solvent removed under vacuum
extractionThe suspension was extracted with ethyl acetate (3×50 mL)
customdried
customthe solvent removed
customto yield a white solid
customThe solid was triturated with diethyl ether (2×25 mL)
customthe solvent decanted
customthe residue dried under vacuum

Sources & evidence

ORD record: ord-b88c3a703bcc488dbc932d98c74a8a3b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115132B2

Reaction notes

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