87237-65-8

Basic information

• Product Name: 3-acetoxy-3-(1-acetoxy-1-methylethyl)-1,4-dibenzylpiperazine-2,5-dione
• CAS NO: 87237-65-8
• Molecular Weight: 452.507
• Mol File: 87237-65-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-acetoxy-3-(1-acetoxy-1-methylethyl)-1,4-dibenzylpiperazine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetoxy-3-(1-acetoxy-1-methylethyl)-1,4-dibenzylpiperazine-2,5-dione(87237-65-8)
• EPA Substance Registry System: 3-acetoxy-3-(1-acetoxy-1-methylethyl)-1,4-dibenzylpiperazine-2,5-dione(87237-65-8)

Safety Data

• Hazardous Substances Data: 87237-65-8(Hazardous Substances Data)

Upstream product

• 6499-33-8 3-isopropylidenepiperazine-2,5-dione 
• 87237-67-0 1,4-dibenzyl-3-hydroxy-3-(1-p-toluenesulfonoxy-1-methylethyl)piperazine-2,5-dione 
• 87237-70-5 1,4-dibenzyl-3-(1-bromo-1-methylethyl)-3-hydroxypiperazine-2,5-dione 
• 87237-64-7 1,4-dibenzyl-3-isopropylidene-2,5-piperazinedione 
• 5369-63-1 ethyl 3,3-dimethyl-oxirane-2-carboxylate 
• 21195-44-8 ethyl 2-<(chloroacetyl)amino>-3-methyl-2-butenoate 
• 20201-24-5 ethyl 3-methyl-2-oxobutanoate 
• 33537-17-6 ethyl 2-hydroxy-3-methyl-3-butenoate 
• 2441-06-7 ethyl 2-hydroxy-3-methylbutanoate 
• 108-24-7 acetic anhydride 
• 87237-63-6 4,7-dibenzyl-2,2-dimethyl-1-oxa-4,7-diazaspiro<2.5>octane-5,8-dione 

Relevant articles and documents

Synthesis of piperazine-2,5-diones related to bicyclomycin: 1,4-dibenzyl-3-hydroxy-3-piperazine-2,5-dione. 2. Route via cyclic intermediates

1,4-Dibenzyl-3-hydroxy-3-piperazine-2,5-dione (43),which incorporates several of the structural features of the antibiotic bicyclomycin, has been synthesized via a reaction sequence involving early construction of the piperazine-2,5-dione ring.In model studies 3-isopropylidenepiperazine-2,5-dione was di-N-benzylated and epoxidized to give 4,7-dibenzyl-2,2-dimethyl-1-oxa-4,7-diazaspirooctane-5,8-dione (10).The opening of the epoxide ring of 10 by several reagents was investigated and it was found that treatment with magnesium isopropylcyclohexylamide (MICA) gives 1,4-dibenzyl-3-hydroxy-3-(1-methylethenyl)piperazine-2,5-dione (23).Treatment of ethyl 3-(2-methoxyethyl)-3-methyl-glycidate (28) with p-toluenesulfonic acid followed by hydrogenation and oxidation gives ethyl 5-methoxy-3-methyl-2-oxopentanoate, which on reaction with chloroacetamide and sulfuric acid followed by treatment of the resulting enamide with ammonia gives (Z)- and (E)-3-(4-methoxybut-2-ylidene)piperazine-2,5-dione.Di-N-benzylation of these followed by epoxidation gives (Z)- and (E)-4,7-dibenzyl-2-(2-methoxyethyl)-2-methyl-1-oxa-4,7-diazaspirooctane-5,8-dione (41 and 42).Treatment of 41 with MICA converts it to compound 43.Chromatography of 43 on silica converts it in part to N-benzyl-N-(2-benzylamino-2-oxoethyl)-3-(2-methoxyethyl)-2-oxo-3-butenamide, which on treatment with MICA regenerates 43.