ChemicalBook CAS DataBase List p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate synthesis

6synthesis methods

Product Name:p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate
CAS Number:74288-40-7
Molecular formula:C16H16N2O7
Molecular Weight:348.31

74288-39-4 Synthesis

2-Azetidinebutanoic acid, a-diazo-3-(1-hydroxyethyl)-b,4-dioxo-, (4-nitrophenyl)Methyl ester, [2R-[2a,3b(R*)]]-

74288-39-4
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p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

74288-40-7
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Yield:-

Reaction Conditions:

rhodium (II) octanoate dimer in dichloromethane; for 4 - 5 h;Heating / reflux;

Steps:

3

(3S, 4R)-3- [ (LR)-HYDROXYETHYL]-4- [3- (4-NITROBENZYLOXY) CARBONYL-2-OXO-3- diazopropyl] azetidin-2-one (250 g) and rhodium octanoate dimmer (1.0 g) were added to dichloromethane (2.5 L) and heated to reflux for 4 to 5 hours. The reaction was monitored by HPLC until unreacted azetidinone was not more than 2.0%. To the clear dichloromethane solution, cyclohexane was added to precipitate the product at 20 °C to 30 °C. The product was filtered, washed with cyclohexane and dried. Yield: 188g

References:

WO2005/21560,2005,A1 Location in patent:Page/Page column 13