Hydrochloric Acid → (S)-2-(6-(5-(3-(2-Chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

HRID 403986Notes

Reaction equation

HRID 403986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:35])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:25]=[C:24]3[C:20]([CH2:21][N:22]([C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30]C)=[O:29])[C:23]3=[O:26])=[CH:19][CH:18]=2)=[N:15][CH:16]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:35])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:25]=[C:24]3[C:20]([CH2:21][N:22]([C@@H:27]([CH:32]([CH3:33])[CH3:34])[C:28]([OH:30])=[O:29])[C:23]3=[O:26])=[CH:19][CH:18]=2)=[N:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 131731549(S)-Methyl 2-(6-(5-(3-(2-chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 70975553(S)-2-(6-(5-(3-(2-Chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of example 393 (75 mg, 0.150 mmol) was taken in THF (3 mL) and MeOH (1 mL) and to this reaction mixture, 1 N LiOH (31.47 mg, 0.75 mmol) was added and stirred at room temperature for 2-3 h. After completion of the reaction, 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, solvent
  2. customwas evaporated
  3. customthe residue obtained

Sources & evidence

ORD record
ord-eee15b1a947b4393a25199968ebef1f0
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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