Lithium Hydroxide → HCID 59497281, compound

HRID 1747441Notes

Reaction equation

HRID 1747441 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[N:28]3[C:23]([CH:24]=[CH:25][CH:26]=[C:27]3[CH3:29])=[C:22]([C:30]#[N:31])[CH:21]=2)[C:11]1=[O:32])[CH2:7][CH2:8][CH3:9])C.[Li+].[OH-]>O1CCOCC1.O>[C:30]([C:22]1[CH:21]=[C:20]([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])[N:28]2[C:23]=1[CH:24]=[CH:25][CH:26]=[C:27]2[CH3:29])#[N:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59497636HCID 59497636, compound

Product 1

HCID 59497281HCID 59497281, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[3-(1-Cyano-5-methyl-indolizin-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (30 mg, 0.067 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was added LiOH (3.2 mg, 0.14 mmol) at room temperature. The solution was stirred at the same temperature for 12 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 precipitate out from the solution was collected by filtration. The solid was dried under vacuum and was confirmed to be the desirable product 1 (19 mg, 67%). LCMS (ESMS): m/z 417.28 (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 precipitate out from the solution was collected by filtration
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-cf9caed96f5745a4be646cc8ae56a240
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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