Sodium Nitrite → HCID 178514119, compound

HRID 444550Notes

Reaction equation

HRID 444550 reaction equation
[Br:1][CH2:2][C:3](=[O:25])[CH2:4][C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].[N:26]([O-])=[O:27].[Na+]>C(O)(=O)C>[Br:1][CH2:2][C:3](=[O:25])[C:4](=[N:26][OH:27])[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 886069703-Carbamoyloxymethyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 178514119HCID 178514119, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

While a solution of 0.15 g of 7-(4-bromo-3-oxobutyrylamino)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid in 2 ml of acetic acid was stirred at room temperature, 0.03 g of sodium nitrite was added dropwise over a period of five minutes. Then, the mixture was further stirred for 20 minutes, after which time it was concentrated to dryness under reduced pressure. The resultant vitreous solid was applied to a Merck silica gel plate No. 5715 and developed with ethyl acetate-acetic acid-water (8:1:1). The color reaction with a 0.5% solution of copper chloride gave a single yellow spot at Rf=0.327. Therefore, the product was assumed to be substantially the captioned compound and was subjected to the next reaction.

Workup

  1. concentrationafter which time it was concentrated to dryness under reduced pressure
  2. customThe color reaction with a 0.5% solution of copper chloride
  3. customgave a single yellow spot at Rf=0.327
  4. customwas subjected to the next reaction

Sources & evidence

ORD record
ord-81bc826b964b494da1923eff202b6c5b
Source dataset
uspto-grants-1981_04
Patent number
US04264595

Reaction notes

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