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 2059645Notes

Reaction equation

HRID 2059645 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-471dc8161f724fff9c4200623cc6d748
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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