Hydrogen Peroxide → HCID 131715691, compound

HRID 34986Notes

Reaction equation

NC(C(O)=O)CCC[C:6]([NH:8][C:9]1([NH:29][CH:30]=[O:31])[C:27](=[O:28])[N:11]2[C:12]([C:24]([OH:26])=[O:25])=[C:13]([CH2:16][S:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH2:14][S:15][C@H:10]12)=[O:7].OO.[N-]=[N+]=[N-].[Na+].P([O-])([O-])([O-])=O>>[C:24]([CH2:12][CH2:13][CH2:14][C:6]([NH:8][C:9]1([NH:29][CH:30]=[O:31])[C:27](=[O:28])[N:11]2[C:12]([C:24]([OH:26])=[O:25])=[C:13]([CH2:16][S:17][C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[CH2:14][S:15][C@H:10]12)=[O:7])([OH:26])=[O:25]

Participants

Reactant 4

HCID 784Hydrogen Peroxide

HCID 1061Phosphate

HCID 33557Sodium Azide

HCID 131715692HCID 131715692, compound

Product 1

HCID 131715691HCID 131715691, compound

Procedure

7-(5-Amino-5-carboxyvaleramido)-7-formylamino-3-(pyridin-4-yl)thiomethyl-3-cephem-4-carboxylic acid obtained in Example 2 was diluted to make a solution showing the inhibition zone diameter of 20 mm against Proteus sp. SS-12 by the paper disc method. The solution was adjusted to pH of 7.5. To 30 μl of the solution were added 12 μl of a 1% aqueous hydrogen peroxide solution, 12 μl of a 1% sodium azide aqueous solution and 18 μl of a solution obtained by diluting D-amino acid oxidase derived from Trigonopsis variabilis (IFO 0755, IFO 0671, cf. U.S. Pat. No. 4,242,449) with a 0.02M phosphate buffer solution (pH 7.0) in 40,000 units/ml. The thus obtained solution was reacted at 37° C. for 1 hour to give 7-(4-carboxybutyramido)-7-formylamino-3-(pyridin-4-yl)thiomethyl-3-cephem-4-carboxylic acid.

Workup

customobtained
customThe thus obtained solution was reacted at 37° C. for 1 hour

Sources & evidence

ORD record: ord-48cb6afc8c6c4616b0b1d395bf5fb411
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04764606

Reaction notes

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