Lithium Hydroxide → HCID 59497611, compound

HRID 1747476Notes

Reaction equation

HRID 1747476 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH2:18][C:19](=[O:26])[NH:20]3)[C:7]1=[O:27].[OH-].[Li+]>O.O1CCOCC1>[Cl:25][C:23]1[CH:22]=[C:21]2[C:17]([CH2:18][C:19](=[O:26])[NH:20]2)=[C:16]([CH2:15][N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]([CH2:5][CH2:4][C:3]([OH:28])=[O:2])[C:7]2=[O:27])[CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67360378HCID 67360378, compound

Product 1

HCID 59497611HCID 59497611, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

3-[3-(6-Chloro-2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (34 mg 0.09 mmol) is dissolved in dioxane water (2 mL/2 mL) and lithium hydroxide (18 mg, 0.45 mmol) is added in one portion. The reaction is stirred for one hour then the solvents evaporated in vacuo. The crude material is purified by preparative reverse phase LC to give the title compound (12 mg 0.03 mmol, 36%). LCMS (ESMS): m/z 387.1 (M+H+).

Workup

  1. customthe solvents evaporated in vacuo
  2. customThe crude material is purified by preparative reverse phase LC

Sources & evidence

ORD record
ord-f9ed6f589a7f408b99d44975ba774f83
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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