Sodium Bicarbonate → HCID 70505182, compound

HRID 1463145Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:26](=[O:27])[N:12]2[C:13]([C:23]([OH:25])=[O:24])=[C:14]([CH2:18]OC(=O)C)[C@H:15]([CH3:17])[S:16][C@H:11]12)=[O:8].C([O-])(O)=O.[Na+:32].[CH3:33][N:34]1[C:38]([SH:39])=[N:37][N:36]=[N:35]1>P(=O)(O)(O)O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:26](=[O:27])[N:12]2[C:13]([C:23]([O-:25])=[O:24])=[C:14]([CH2:18][S:39][C:38]3[N:34]([CH3:33])[N:35]=[N:36][N:37]=3)[C@H:15]([CH3:17])[S:16][C@H:11]12)=[O:8].[Na+:32]

Participants

Conditions

Temperature: 50 °C

Procedure

In 20 ml of 1/15M phosphoric acid buffer solution (pH 6.4) were dissolved 410 mg of 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylic acid and 84 mg of NaHCO3, and 139 mg of 1-methyl-5-mercaptotetrazole was then added to the solution. The reaction solution was stirred at 50° C. for 6 hours, while maintaining it at pH 6.4 by pouring 5% aqueous NaHCO3, and then added on a column of Amberlite XAD-II (produced by Rohm & Haas), followed by washing with water and eluting by the gradient method with 0 to 70% aqueous methanol. The eluted fractions were collected, concentrated under reduced pressure and freeze-dried, thus yielding 148 mg (30%) of sodium 7-(2-thienylacetamido)-2β-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate.

Workup

additionwas then added to the solution
temperaturewhile maintaining it at pH 6.4
additionadded on a column of Amberlite XAD-II (produced by Rohm & Haas)
washby washing with water
washeluting by the gradient method with 0 to 70% aqueous methanol
customThe eluted fractions were collected
concentrationconcentrated under reduced pressure
customfreeze-dried

Sources & evidence

ORD record: ord-7e59503f8d2f46b1aa3871ba5b6f843f
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04463172

Reaction notes

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