Tetrahydrofuran → HCID 19833181, compound

HRID 1639391Notes

Reaction equation

HRID 1639391 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[C:9]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:8]=2[CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][C:5]1=[O:26])(=[O:3])[CH3:2].[O:27]1CCCC1>Cl>[C:1]([NH:4][CH2:13][CH2:12][CH2:11][C:10]([C:9]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:8]=1[CH:7]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:6][C:5]([OH:27])=[O:26])=[O:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 19833151HCID 19833151, compound

Product 1

HCID 19833181HCID 19833181, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3.30 g (0.009 mol) of 4-acetyl-11-chloro-1-phenyl-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione in 40 ml of tetrahydrofuran and 20 ml of 2N hydrochloric acid is stirred at room temperature for two days. Then, the solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with hexane-ethyl acetate (1:1) and crystallization from ethyl acetate/hexane gives 2-(4-acetamidobutyryl)-5-chloro-β-phenylhydrocinnamic acid as white crystals with melting point 114°-116°.

Workup

  1. concentrationThen, the solution is concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customChromatography on silica gel with hexane-ethyl acetate (1:1) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-560e58a2007f47e785c5121ac8accc53
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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