2,6-Lutidine → (6R,7R)-2,2-dimethyl-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 1719317Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:13])[C@@H:5]2[NH:10][CH:11]=O.N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:14])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:13])[C@@H:5]2[N+:10]#[C-:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (345 mg) were added 2,6-lutidine (2.05 ml) and phosphorus oxychloride (0.52 ml) at 0° C. After stirring for 3 hours at 0° C., the mixture was poured into a mixture of ethyl acetate (80 ml) and ice-water. The organic layer was separated, washed in turn with 10% phosphoric acid, water, brine, an aqueous mixture of sodium bicarbonate and sodium chloride (1:1), and brine, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was washed with a mixture of petroleum ether and ether (1:1) and dried over phosphorus pentoxide to give (6R,7R)-2,2-dimethyl-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one (205 mg).

Workup

customThe organic layer was separated
washwashed in turn with 10% phosphoric acid, water, brine
additionan aqueous mixture of sodium bicarbonate and sodium chloride (1:1), and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
washThe crystalline residue was washed with a mixture of petroleum ether and ether (1:1)
dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record: ord-2d8e23020da144a6a2c64e5973a120d3
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539152

Reaction notes

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