Hydrochloric Acid → 2-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

HRID 1639366Notes

Reaction equation

HRID 1639366 reaction equation
Cl.[C:2]([N:5]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:10]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:9]=2[CH2:8][CH2:7][C:6]1=[O:21])(=[O:4])[CH3:3].[O:22]1CCCC1>>[C:2]([NH:5][CH2:14][CH2:13][CH2:12][C:11]([C:10]1[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:9]=1[CH2:8][CH2:7][C:6]([OH:21])=[O:22])=[O:15])(=[O:4])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 198331174-Acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

Product 1

HCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Procedure

500 ml of 2N hydrochloric acid are added to a solution of 103 g (0.35 mol) of 4-acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione in 1 l of tetrahydrofuran and the mixture is stirred at room temperature overnight. The mixture is concentrated in a vacuum, treated with methylene chloride and extracted twice with 2N sodium hydroxide solution; the aqueous phase is then acidified with 6N hydrochloric acid and extracted with methylene chloride. Removal of the solvent by distillation in a vacuum and chromatography on silica gel with methylene chloride/methanol (20:1) yields 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid with melting point 90°-92°.

Workup

  1. concentrationThe mixture is concentrated in a vacuum
  2. additiontreated with methylene chloride
  3. extractionextracted twice with 2N sodium hydroxide solution
  4. extractionextracted with methylene chloride
  5. customRemoval of the solvent
  6. distillationby distillation in a vacuum and chromatography on silica gel with methylene chloride/methanol (20:1)

Sources & evidence

ORD record
ord-c0f51c09cdce443684e9162ce2926b8b
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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