Sodium Hydroxide → {5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetic acid

HRID 2074120Notes

Reaction equation

HRID 2074120 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[N:10]=[C:9]([C:20]3[N:21]=[N:22][N:23]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[CH:24]=3)[CH:8]=2)=[CH:4][CH:3]=1.CO.C1COCC1.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([OH:15])=[O:14])[N:10]=[C:9]([C:20]3[N:21]=[N:22][N:23]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)[CH:24]=3)[CH:8]=2)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 68360285tert-butyl {5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetate

Product 1

HCID 67092066{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of tert-butyl {5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetate (14.0 g, 29.3 mmol) in mixed solvent of MeOH/THF (60 mL/20 mL) was added a solution of NaOH (3.5 g, 88 mmol) in H2O (20 mL) and the reaction mixture was stirred at room temperature for an hour. The mixture was evaporated and the residue was diluted with water (100 mL) and washed with EtOAc (2×100 mL). The aqueous layer was adjusted to pH=3-4 with conc. HCl. The precipitate was filtered and dried in vacuo to afford the title compound (11.0 g, 90.0%) as a yellow solid.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with water (100 mL)
  3. washwashed with EtOAc (2×100 mL)
  4. filtrationThe precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d315819b055d41ecaa84f5811852b2fb
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

Loading…