Lithium Hydroxide → 3-{3-[(6,8-dichloro-3-methylindolizin-1-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}hexanoic acid

HRID 1747443Notes

Reaction equation

HRID 1747443 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]=[C:22]([CH3:31])[N:23]3[C:28]=2[C:27]([Cl:29])=[CH:26][C:25]([Cl:30])=[CH:24]3)[C:11]1=[O:32])[CH2:7][CH2:8][CH3:9])C.[Li+].[OH-]>O1CCOCC1.O>[Cl:30][C:25]1[CH:26]=[C:27]([Cl:29])[C:28]2[N:23]([C:22]([CH3:31])=[CH:21][C:20]=2[CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:33])=[O:3])[C:11]2=[O:32])[CH:24]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59497406HCID 59497406, compound

Product 1

HCID 251255583-{3-[(6,8-dichloro-3-methylindolizin-1-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[3-(6,8-Dichloro-3-methyl-indolizin-1-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (20 mg, 0.041 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was added LiOH (2 mg, 0.082 mmol) at room temperature. The solution was stirred at the same temperature for 4 hours. The solution was concentrated and water was added to the residue. The solution was acidified by 12N HCl in an ice-bath. The solid that preciptate out from the solution was collected by filtration. The solid was dried under vacuum and was confirmed to be the desirable product. LCMS (ESMS): m/z 460.17 (M+H+).

Workup

  1. concentrationThe solution was concentrated
  2. additionwater was added to the residue
  3. customThe solution was acidified by 12N HCl in an ice-bath
  4. filtrationThe solid that preciptate out from the solution was collected by filtration
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-40d4cc50a9cf44c58c343733afc03160
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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