Diphenylmethyl (2R)-3-methyl-2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-3-butenoate synthesis
- Product Name:Diphenylmethyl (2R)-3-methyl-2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-3-butenoate
- CAS Number:67977-61-1
- Molecular formula:C28H24N2O4
- Molecular Weight:452.5
Yield:67977-61-1 81.2%
Reaction Conditions:
with triphenylphosphine in water;ethyl acetate;toluene;benzene;
Steps:
I.1 (No. 10)
(No. 10) A solution of 38.51 g of diphenylmethyl 6α-benzamidopenicillanate 1-oxide and 22.11 g of triphenylphosphine in a mixture of 308 ml of toluene and 308 ml of 1,2-dichloroethane is refluxed for 3.5 hours while removing water by means of Dean-Stark type water separator containing Molecular Sieves 5A. After cooling, the reaction mixture is concentrated to 150 ml, purified by chromatography on 500 g of silica gel deactivated with 10% water using a mixture of benzene and ethyl acetate (19:1) and then a mixture of benzene and ethyl acetate (4:1) as eluding solvents. The elude containing the desired product is crystallized from ether to afford 28.15 g of diphenylmethyl (2R)-3-methyl-2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-3-butenoate in 81.2% yield. mp. 116°-118° C.
References:
US4220766,1980,A
69780-18-3
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![4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(benzoylamino)-3,3-dimethyl-7-oxo-, diphenylmethyl ester, 4-oxide, [2S-(2α,4β,5α,6α)]- (9CI)](/CAS/20210305/GIF/73037-40-8.gif)
73037-40-8
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