Sodium Hydroxide → 3-({1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carbonyl}-amino)-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid

HRID 241680Notes

Reaction equation

HRID 241680 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:7]=[C:6]([NH:16][C:17]([CH:19]2[CH2:23][CH2:22][C:21](=[O:24])[N:20]2[CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([CH3:39])[CH:33]=3)[CH2:27][CH2:26]2)=[O:18])[CH:5]=1.[OH-].[Na+]>CO>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:28]2[CH2:27][CH2:26][CH:25]([N:20]3[C:21](=[O:24])[CH2:22][CH2:23][CH:19]3[C:17]([NH:16][C:6]3[CH:5]=[C:4]([CH:9]=[C:8]([C:10]4[N:14]([CH3:15])[N:13]=[N:12][N:11]=4)[CH:7]=3)[C:3]([OH:40])=[O:2])=[O:18])[CH2:30][CH2:29]2)=[CH:33][C:34]=1[CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 667331223-({1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carbonyl}-amino)-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid methyl ester

Product 1

HCID 667334583-({1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carbonyl}-amino)-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acidYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-({1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carbonyl}-amino)-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid methyl ester (270 mg) in MeOH (10 ml) at room temperature was added 4M NaOH(aq) (10 ml) and the reaction stirred overnight. The organic and aqueous layers were separated and the organic layer concentrated in vacuum. The residue was triturated in toluene and diethyl ether successively leaving the title compound (220 mg). Rt=0.96 min (method E).

Workup

  1. customThe organic and aqueous layers were separated
  2. concentrationthe organic layer concentrated in vacuum
  3. customThe residue was triturated in toluene

Sources & evidence

ORD record
ord-f218c26f53f5499f82ba372df896bfab
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

Loading…