Lithium Hydroxide → (R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid

HRID 2175182Notes

Reaction equation

HRID 2175182 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N:15]([CH2:22][C:23]2[C:27]3[C:28]([CH3:33])=[CH:29][C:30]([CH3:32])=[CH:31][C:26]=3[S:25][N:24]=2)[C:14]1=[O:34])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Li+]>O1CCOCC1.O>[CH3:33][C:28]1[C:27]2[C:23]([CH2:22][N:15]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:21]=4[N:13]([C@@H:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:5][C:4]([OH:35])=[O:3])[C:14]3=[O:34])=[N:24][S:25][C:26]=2[CH:31]=[C:30]([CH3:32])[CH:29]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58497400(R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497409(R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-3-[3-(4,6-dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester (10 mg, 0.021 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was added lithium hydroxide (LiOH) (0.9 mg, 0.042 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 solution was concentrated and the residue was purified by preparative TLC with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (8.3 mg, 88%): LCMS, M++1, m/z: 459.13 as a white solid.

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. concentrationThe solution was concentrated
  5. customthe residue was purified by preparative TLC with 10% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-160a8cdcf5d34b6bae25bc091935e539
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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