Hydrochloric Acid → 3-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid

HRID 1971322Notes

Reaction equation

HRID 1971322 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH:5]([N:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>[OH-].[Na+].CO>[O:21]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][N:12]1[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][C:3]([OH:22])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68443776HCID 68443776, compound

Product 1

HCID 188709533-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

3-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid methyl ester (0.5 mmol, 1 eq) is dissolved in 8 mL 1 M NaOH/MeOH (25% V/V) and stirred at room temperature for 2 h. The solution is acidified with 1 M HCl and extracted with dichloromethane. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. 3-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid is obtained as red-orange residue (81% yield); ES-MS (MH+)=282.2.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e5467260d1c4d37b5c5d3927a529ca9
Source dataset
uspto-grants-2013_04
Patent number
US08431602B2

Reaction notes

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