Hydrochloric Acid → (S)-2-(6-(5-(4-tert-Butylbenzamido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methyl butanoic acid

HRID 403996Notes

Reaction equation

HRID 403996 reaction equation
[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:26]=[C:25]4[C:21]([CH2:22][N:23]([C@@H:28]([CH:33]([CH3:35])[CH3:34])[C:29]([O:31]C)=[O:30])[C:24]4=[O:27])=[CH:20][CH:19]=3)=[N:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.[Li+].[OH-].Cl>C1COCC1.O>[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:26]=[C:25]4[C:21]([CH2:22][N:23]([C@@H:28]([CH:33]([CH3:34])[CH3:35])[C:29]([OH:31])=[O:30])[C:24]4=[O:27])=[CH:20][CH:19]=3)=[N:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 131731552(S)-Methyl 2-(6-(5-(4-tert-butylbenzamido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 67306402(S)-2-(6-(5-(4-tert-Butylbenzamido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methyl butanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of example 403 (80 mg, 0.160 mmol) was taken in THF (4 mL) and MeOH (1 mL) and to this reaction mixture, 1N LiOH (33.59 mg, 0.800 mmol) was added and stirred at room temperature for 2-3 h. After completion of the reaction, the solvent was evaporated and the residue obtained was dissolved in water and acidified with 1 N HCl to obtain the title compound, which was filtered and dried.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe residue obtained

Sources & evidence

ORD record
ord-278223d8cd3c4f4db5d3b7849f084706
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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