Hydrochloric Acid → HCID 70154184, compound

HRID 2187038Notes

Reaction equation

HRID 2187038 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C@@:7]12[CH2:18][CH2:17][CH2:16][C:14]3[C:15]1=[C:10]([CH:11]=[CH:12][CH:13]=3)[NH:9][C:8]2=[O:19])([OH:3])=[O:2].Cl.[CH:21](OC(C)C)(C)C>CO>[CH3:21][O:2][C:1]([CH2:4][CH2:5][CH2:6][C@@:7]12[CH2:18][CH2:17][CH2:16][C:14]3[C:15]1=[C:10]([CH:11]=[CH:12][CH:13]=3)[NH:9][C:8]2=[O:19])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 70154008HCID 70154008, compound

Product 1

HCID 70154184HCID 70154184, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2a-(3-carboxypropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (7.00 g, 27 mmol) was dissolved in methanol (200 ml). Then, 36% hydrochloric acid 0.1 ml was added thereto and stirred at room temperature for two days. The solvent was evaporated from the reaction mixture, and ethyl acetate and water were added to the resulting residue. A reaction product was extracted with ethyl acetate, and the extracted product was washed with saturated saline solution, successively dried over anhydrous sodium sulfate, followed by evaporating the solvent. The resulting product was crystallized from diisopropyl ether, whereby 6.89 g (yield 93%) of the above-described object compound could be obtained.

Workup

  1. customThe solvent was evaporated from the reaction mixture, and ethyl acetate and water
  2. additionwere added to the resulting residue
  3. extractionA reaction product was extracted with ethyl acetate
  4. washthe extracted product was washed with saturated saline solution
  5. dry with materialsuccessively dried over anhydrous sodium sulfate
  6. customby evaporating the solvent

Sources & evidence

ORD record
ord-cde5fb0bfd5e4cca9e8036a4eccd8018
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

Loading…