Hydrochloric Acid → (S)-2-(5-(4-(3-(4-Fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

HRID 403863Notes

Reaction equation

HRID 403863 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:35])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[N:21]([C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30]C)=[O:29])[CH2:20]4)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:35])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[N:21]([C@@H:27]([CH:32]([CH3:33])[CH3:34])[C:28]([OH:30])=[O:29])[CH2:20]4)=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 123620640(S)-Methyl 2-(5-(4-(3-(4-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 67306564(S)-2-(5-(4-(3-(4-Fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of example 224 (0.500 g, 0.00102 mol) was taken in THF (8 mL) and MeOH (1 mL) and to this reaction mixture, 1 N LiOH (0.213 g, 0.0051 mol) 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-5012a614bc224cebb6a6ec452d069024
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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