Sodium Bicarbonate → Cefamandole sodium

HRID 1660637Notes

Reaction equation

[C:1]([NH:11][C@@H:12]1[C:31](=[O:32])[N:14]2[C:15]([C:28]([OH:30])=[O:29])=[C:16]([CH2:19]OC(=O)CCC(O)=O)[CH2:17][S:18][C@H:13]12)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[SH:33][C:34]1[N:38]([CH3:39])[N:37]=[N:36][N:35]=1.C(=O)([O-])O.[Na+:44]>O>[Na+:44].[C:1]([NH:11][C@@H:12]1[C:31](=[O:32])[N:14]2[C:15]([C:28]([O-:30])=[O:29])=[C:16]([CH2:19][S:33][C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)[CH2:17][S:18][C@H:13]12)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

Conditions

Temperature: 60 °C

Procedure

In water (5 ml) was dissolved 7β-(D-mandelamido)-3-(3-carboxypropionyloxy)methyl-3-cephem-4-carboxylic acid (0.46 g) together with 5-mercapto-1-methyl-1H-tetrazole (0.12 g) and sodium hydrogen carbonate (0.25 g). The solution was stirred at 60° C. for 1 hour and a half. After cooling in the air, the reaction mixture was subjected to column chromatography on Amberlite XAD-2, elution being carried out with water and, then, with a solvent mixture of water and methanol. The fractions containing the desired compound are pooled, concentrated and lyophilized. The procedure provided 7β-(D-mandelamido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid sodium salt (0.31 g)

Workup

temperatureAfter cooling in the air
washthe reaction mixture was subjected to column chromatography on Amberlite XAD-2, elution
additionwith a solvent mixture of water and methanol
additionThe fractions containing the desired compound
concentrationconcentrated

Sources & evidence

ORD record: ord-b32ef3a629844ca7b0156e2a5e211bb4
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04308381

Reaction notes

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