2-Azidoethyl trifluoromethanesulfonate → 3-Cephem-4-carboxylate trifluoromethanesulfonate

HRID 704275Notes

Reaction equation

C(NC1SC=C(C(=NOC)C(N[CH:13]2[C:45](=[O:46])[N:15]3[C:16]([C:29]([O:31]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:30])=[C:17](S/C=C\C4C=NC=CC=4)[CH2:18][S:19][C@H:14]23)=O)N=1)=O.[F:50][C:51]([F:62])([F:61])[S:52]([O:55]CCN=[N+]=[N-])(=[O:54])=[O:53]>CN(C)C=O>[F:50][C:51]([F:62])([F:61])[S:52]([OH:55])(=[O:54])=[O:53].[S:19]1[C@@H:14]2[CH2:13][C:45](=[O:46])[N:15]2[C:16]([C:29]([OH:31])=[O:30])=[CH:17][CH2:18]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (syn isomer) (2 g) in N,N-dimethylformamide (10 ml) was added 2-azidoethyl trifluoromethanesulfonate (2.4 g) at ambient temperature, and the mixture was stirred at 40° C. for 3 hours and then at ambient temperature through the night. The mixture was evaporated in vacuo to give a residue. The residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and tetrahydrofuran (1:1). The fractions containing the object compound were combined and evaporated in vacuo to give benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(Z)-2-{1-(2-azidoethyl)-3-pyridinio}vinylthio]-3-cephem-4-carboxylate trifluoromethanesulfonate (syn isomer) (1.36 g).

Workup

customat ambient temperature
customThe mixture was evaporated in vacuo
customto give a residue
washeluted with a mixture of ethyl acetate and tetrahydrofuran (1:1)
additionThe fractions containing the object compound
customevaporated in vacuo

Sources & evidence

ORD record: ord-977ec83fa702403bb120286a13b465bc
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985555

Reaction notes

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