Oxalyl chloride → Pivaloyloxymethyl 7-[(4-(3-azidopropyl)-1-piperidyl)-methyleneamino]-3-methyl-3-cephem-4-carboxylate

HRID 128209Notes

Reaction equation

[CH:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][N:12]=[N+:13]=[N-:14])[CH2:5][CH2:4]1)=O.C(Cl)(=O)C(Cl)=O.[NH2:21][CH:22]1[C:41](=[O:42])[N:24]2[C:25]([C:30]([O:32][CH2:33][O:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:31])=[C:26]([CH3:29])[CH2:27][S:28][C@H:23]12>C(N(CC)CC)C>[N:12]([CH2:11][CH2:10][CH2:9][CH:6]1[CH2:7][CH2:8][N:3]([CH:1]=[N:21][CH:22]2[C:41](=[O:42])[N:24]3[C:25]([C:30]([O:32][CH2:33][O:34][C:35](=[O:40])[C:36]([CH3:37])([CH3:38])[CH3:39])=[O:31])=[C:26]([CH3:29])[CH2:27][S:28][C@H:23]23)[CH2:4][CH2:5]1)=[N+:13]=[N-:14]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of N-formyl-4-(3-azidopropyl)-piperidine (1.13 g) in alcohol-free chloroform (2.5 ml) was cooled to -20° C. and oxalyl chloride (0.44 ml) in alcohol-free chloroform (2.5 ml) was added dropwise. After 1 hour at -20° C. the solution was added dropwise at -60° C. to -70° C. to a stirred solution of pivaloyloxymethyl 7-amino-3-methyl-3-cephem-4-carboxylate (1.72 g) in alcohol-free chloroform (12 ml). Triethylamine (1.46 ml) was added and within the next hour the temperature was gradually raised to -10° C. The solvent was evaporated and the residue was extracted with ether. The ether extract was evaporated to leave an oil, which was purified by column chromatography on Sephadex to yield the desired compound as a yellow oil.

Workup

customThe solvent was evaporated
extractionthe residue was extracted with ether
extractionThe ether extract
customwas evaporated
customto leave an oil, which
customwas purified by column chromatography on Sephadex

Sources & evidence

ORD record: ord-373c942d19a845488de9d8032787a560
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04259333

Reaction notes

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