Lithium hydroxide, monohydrate → 5-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid

HRID 77770Notes

Reaction equation

HRID 77770 reaction equation
O[Li].O.C[O:5][C:6]([C:8]1[CH:9]=[C:10]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH:11]=[C:12]([C:14]2[N:18]([CH2:19][CH3:20])[N:17]=[N:16][N:15]=2)[CH:13]=1)=[O:7]>O.C1COCC1>[CH2:19]([N:18]1[C:14]([C:12]2[CH:13]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[CH:11]=2)=[N:15][N:16]=[N:17]1)[CH3:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 578516285-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 578512625-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acidYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (39.1 mg, 0.931 mmol) in H2O (8 mL) was added dropwise to a suspension of 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (200 mg, 0.621 mmol) in THF (5 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred until the mixture turned clear. THF was removed under vacuum and the aqueous solution was acidified by 10% HCl to pH=3. The precipitate was collected and dried to afford 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid as white solid (162 mg, 84%). MS (M+H)=309.

Workup

  1. customTHF was removed under vacuum
  2. customThe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-8891473a1186456c8ce21540cff1542b
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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