Acetic-formic anhydride → (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 851411Notes

Reaction equation

[NH2:1][C@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[CH2:4][CH2:5][O:6][C:7]2([CH3:12])[CH3:11].[CH:13](OC(=O)C)=[O:14]>N1C=CC=CC=1>[CH3:11][C:7]1([CH3:12])[O:6][CH2:5][CH2:4][C@H:3]2[N:8]1[C:9](=[O:10])[C@@H:2]2[NH:1][CH:13]=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (300 mg) were added pyridine (0.25 ml) and freshly prepared acetic formic anhydride (0.38 ml) at 0° C. After stirring for 45 minutes at 0° C., the reaction mixture was evaporated in vacuo. The residue was dissolved in xylene and the solution was evaporated in vacuo. The residue was chromatographed on silica gel (6 g) eluting with a mixture of methylene chloride and methanol (25:1-10:1) to give (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (378 mg) as an oil.

Workup

customthe reaction mixture was evaporated in vacuo
dissolutionThe residue was dissolved in xylene
customthe solution was evaporated in vacuo
customThe residue was chromatographed on silica gel (6 g)
washeluting with a mixture of methylene chloride and methanol (25:1-10:1)

Sources & evidence

ORD record: ord-faa707e819e94ef0b6a6f3669eb0b63d
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04383945

Reaction notes

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