Lithium Hydroxide → 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid

HRID 1747365Notes

Reaction equation

HRID 1747365 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:28]=2[N:27]([CH3:29])[C:26]([CH3:30])=[C:25]3[CH3:31])[C:11]1=[O:32])[CH2:7][CH2:8][CH3:9])C.[Li+].[OH-]>O1CCOCC1.O>[O:32]=[C:11]1[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:33])=[O:3])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]1[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:28]=1[N:27]([CH3:29])[C:26]([CH3:30])=[C:25]2[CH3:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 594972503-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester

Product 1

HCID 594972853-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acidYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester (50 mg, 0.11 mmol) in 1,4-dioxane (5 mL) and H2O (2 mL) was added LiOH (5.4 mg, 0.22 mmol). The solution was stirred at room temperature for 5 hours. The solution was concentrated and the residue was purified by CombiFlash with 10% MeOH in CH2Cl2 as the eluent to afford the desirable product 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid (14.5 mg, 31%) as a white foam. LC-MS (M++1): 420.21.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by CombiFlash with 10% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-dca3a6ef4e824d70ad1b7e24b6474131
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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