Sodium Hydroxide → sodium (S)-3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoate

HRID 1747394Notes

Reaction equation

HRID 1747394 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C@@H:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([OH:26])=[O:25])[C:14]2=[O:30])=[CH:3]1.[OH-].[Na+:32]>O>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C@@H:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([O-:26])=[O:25])[C:14]2=[O:30])=[CH:3]1.[Na+:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25127851(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid

Product 1

HCID 67359360sodium (S)-3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoateYield 102.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (S)-3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (1.45 g, 3.6 mmol) in H2O (25 mL) was added NaOH (1.041 M in THF) (3.1 mL, 3.2 mmol). The solution was stirred at room temperature for 2 hours. The solution was washed with EtOAc (30 mL×2) and the aqueous layer was lyophilized to give the desired sodium (S)-3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoate (1.4 g, 91%) as a white solid. LCMS (ESMS):428.10 (M+H+).

Workup

  1. washThe solution was washed with EtOAc (30 mL×2)

Sources & evidence

ORD record
ord-19aad91546f641e4897dd271d51ccd8c
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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