Reaction #56306

ord-b922538a62834907a1641f96b953c8c3

Reaction equation

CC1(C)OCCC2C(NC(=O)Cc3ccccc3)C(=O)N21
7-phenylacetamido-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo-[4.2.0]octane
CC1(C)OCCC2C(NC(=O)Cc3ccccc3)C(=O)N21
7-amino-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane
CC1(C)OCCC2C(NC(=O)Cc3ccccc3)C(=O)N21
7-phenylacetamido-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane
NC1C(=O)N(C2CCCCO2)C1CCOC1CCCCO1
1-(2-tetrahydropyranyl)-3-amino-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone
→
O=C(Cc1ccccc1)NC1C(=O)N(C2CCCCO2)C1CCOC1CCCCO1
1-(2-tetrahydropyranyl)-3-phenylacetamido-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

Reactants

CC1(C)OCCC2C(NC(=O)Cc3ccccc3)C(=O)N21
7-phenylacetamido-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo-[4.2.0]octane
CC1(C)OCCC2C(NC(=O)Cc3ccccc3)C(=O)N21
7-amino-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane
CC1(C)OCCC2C(NC(=O)Cc3ccccc3)C(=O)N21
7-phenylacetamido-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane
NC1C(=O)N(C2CCCCO2)C1CCOC1CCCCO1
1-(2-tetrahydropyranyl)-3-amino-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following the procedure described for the preparation of 7-phenylacetamido-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo-[4.2.0]octane from 7-amino-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane (Example 6) and using 1-(2-tetrahydropyranyl)-3-amino-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone there is obtained 1-(2-tetrahydropyranyl)-3-phenylacetamido-4-[2-(2-tetrahydropyranyl)oxyethyl]-2-azetidinone.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04224336uspto-grants-1980_09