Hydrochloric Acid → Benzenepropanoic acid, 2-(4-((4-(acetylamino)-1-oxobutyl)amino)-1-oxobutyl)-5-chloro-, ethyl ester
Reaction equation
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][C:6]2[C:7](=[O:25])[CH2:8][CH2:9][CH2:10][N:11]([C:16]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23])=[O:17])[C:12](=[O:15])[CH2:13][CH2:14][C:5]=2[CH:4]=1.[CH2:28]([OH:30])[CH3:29]>C(Cl)Cl>[C:22]([NH:21][CH2:20][CH2:19][CH2:18][C:16]([NH:11][CH2:10][CH2:9][CH2:8][C:7]([C:6]1[CH:26]=[CH:27][C:3]([Cl:2])=[CH:4][C:5]=1[CH2:14][CH2:13][C:12]([O:30][CH2:28][CH3:29])=[O:15])=[O:25])=[O:17])(=[O:24])[CH3:23]Participants
5
Procedure
1 ml of concentrated hydrochloric acid is added to a solution of 2.66 g (0.007 mol) of N-[3-[(11-chloro-2,3,5,6,7,8-hexahydro-3,8-dioxo-4-benzazecin-4-(1H)-yl)carbonyl]propyl]acetamide in 100 ml of ethanol and 30 ml of methylene chloride and the mixture is stirred at room temperature for 5 days. The solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on aluminum oxide with ethyl acetate/ethanol (19:1) and crystallization from methylene chloride/ether gives ethyl 2-[4-(4-acetamidobutyramido)butyryl]-5-chlorohydrocinnamate as white crystals with melting point 95°.
Workup
- concentrationThe solution is concentrated
- extractionextracted with methylene chloride/water
- dry with materialdried with magnesium sulfate
- distillationthe solvent is distilled in a vacuum
- customChromatography on aluminum oxide with ethyl acetate/ethanol (19:1) and crystallization from methylene chloride/ether
Sources & evidence
- ORD record
- ord-8984448ff2e8419797139ddfe47cf588
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04883815
Reaction notes
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