Hydrochloric Acid → (S)-2-(6-(4-(3-(2-Fluorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

HRID 403735

Reaction equation

HRID 403735 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:35])[NH:10][C:11]1[CH:16]=[CH:15][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)=[CH:13][CH:12]=1.[Li+].[OH-].Cl>C1COCC1.CO.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:35])[NH:10][C:11]1[CH:16]=[CH:15][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)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53303391(S)-Methyl 2-(6-(4-(3-(2-fluorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 87349957(S)-2-(6-(4-(3-(2-Fluorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of example 51 (0.224 g, 0.000456 mol) was taken in THF (4 mL) and MeOH (1 mL). To this reaction mixture, 1 N LiOH (0.095 g, 0.0022 mol) was added and the reaction mixture was 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-539fa08f9c5a455ea9477c6cb56f0b1c
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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