Lithium Hydroxide → HCID 59497478, compound

HRID 1747370Notes

Reaction equation

HRID 1747370 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[C:16]2=[O:31])=[C:12]2[C:8]([C:9]([CH3:34])=[C:10]([CH3:33])[N:11]2[CH3:32])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>O1CCOCC1.O>[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:16]2=[O:31])=[C:12]2[C:8]([C:9]([CH3:34])=[C:10]([CH3:33])[N:11]2[CH3:32])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59497255HCID 59497255, compound

Product 1

HCID 59497478HCID 59497478, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-[3-(2-Ethoxycarbonyl-ethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl]-1,2,3-trimethyl-1H-indole-6-carboxylic acid methyl ester (60 mg, 0.13 mmol) in 1,4-dioxane (5 mL) and H2O (2 mL) was added LiOH (6.4 mg). 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 7-[3-(2-Carboxy-ethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl]-1,2,3-trimethyl-1H-indole-6-carboxylic acid methyl ester (10 mg, 17%) as a white solid. LC-MS (M+): 435.36.

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-8f9f54235d9d4ae5bfd3e6927ea5f175
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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