Hydrochloric Acid → 2-[(2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)sulfanyl]acetic acid

HRID 2078473Notes

Reaction equation

HRID 2078473 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][S:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[CH2:17]([N:8]1[C:9](=[O:16])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]1[S:6][CH2:5][C:4]([OH:24])=[O:3])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67096661(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-ylsulfanyl)-acetic acid ethyl ester

Product 1

HCID 29987702-[(2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)sulfanyl]acetic acidYield 41.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 17 (8 gm, 24.5 mmol) in methanol (64 mL) and water (16 mL) at room temperature was added potassium carbonate (5.7 gm, 41.6 mmol) and the resulting reaction mixture was allowed to stir at reflux for 3 hours. The reaction mixture was poured onto 1N HCl and extracted with dichloromethane (3×100 mL). The combined dichloromethane extracts were filtered and the filterate dried over anhydrous sodium sulfate and concentrated in vacuo to provide 3.2 gm of 18 as a pale pink solid (7.8 gm, 41% yield).

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 3 hours
  3. extractionextracted with dichloromethane (3×100 mL)
  4. filtrationThe combined dichloromethane extracts were filtered
  5. dry with materialthe filterate dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5909173183f04bfb8886e4919013b629
Source dataset
uspto-grants-2011_04
Patent number
US07928246B2

Reaction notes

Loading…