437768-95-1

Basic information

• Product Name: (S)-N⁽¹⁾-(p-methoxybenzyl)-6-isopropylpiperazine-2,5-dione
• Synonyms: (S)-N⁽¹⁾-(p-methoxybenzyl)-6-isopropylpiperazine-2,5-dione
• CAS NO: 437768-95-1
• Molecular Weight: 276.335
• Mol File: 437768-95-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-N⁽¹⁾-(p-methoxybenzyl)-6-isopropylpiperazine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N⁽¹⁾-(p-methoxybenzyl)-6-isopropylpiperazine-2,5-dione(437768-95-1)
• EPA Substance Registry System: (S)-N⁽¹⁾-(p-methoxybenzyl)-6-isopropylpiperazine-2,5-dione(437768-95-1)

Safety Data

• Hazardous Substances Data: 437768-95-1(Hazardous Substances Data)

Upstream product

• 1456900-67-6 (S)-methyl 2-(2-chloro-N-(4-methoxybenzyl)acetamido)-3-methylbutanoate 
• 6306-52-1 L-valine methylester hydrochloride 
• 72-18-4 L-valine 
• 938055-35-7 (S)-N-(p-methoxybenzyl)-N-(bromoacetyl)valine methyl ester 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 

Downstream Products

• 437768-96-2 (3S)-1-(o-azidobenzoyl)-4-p-methoxybenzyl-3-isopropylpiperazine-2,5-dione 
• 852994-84-4 (3S)-N-1-(tert-butoxycarbonyl)-N-4-(4-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 938055-36-8 (S)-N⁽¹⁾-methyl-N⁽⁴⁾-(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 
• 72-18-4 L-valine 
• 2462-34-2 L-valine benzyl ester hydrochloride 
• 1456900-73-4 (S)-5-ethoxy-6-isopropyl-1-(4-methoxybenzyl)-1,6-dihydropyrazin-2(3H)-one 
• 1456900-63-2 (S)-2-((R)-2-amino-3-(4-oxocyclohexyl)propanamido)-3-methylbutanoic acid 
• 1456900-77-8 (3R,6S)-5-ethoxy-6-isopropyl-1-(4-methoxybenzyl)-3-((4-oxocyclohexyl)methyl)-1,6-dihydropyrazin-2(3H)-one 
• 1464802-73-0 C₃₀H₅₀N₂O₄Si 

Relevant articles and documents

The synthesis and biological testing of bacilysin analogues

A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.

Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates

Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3, 6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6- dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary α-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis. This journal is The Royal Society of Chemistry.