Hydrochloric Acid → 7-[2-(6-Aminopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 2286632Notes

Reaction equation

HRID 2286632 reaction equation
C([NH:3][C:4]1[N:9]=[C:8]([C:10](=[N:26][O:27][CH3:28])[C:11]([NH:13][CH:14]2[C:24](=[O:25])[N:16]3[C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1)=O.Cl>C(OCC)C>[NH2:3][C:4]1[N:9]=[C:8]([C:10](=[N:26][O:27][CH3:28])[C:11]([NH:13][CH:14]2[C:24](=[O:25])[N:16]3[C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317122227-[2-(6-Formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317122217-[2-(6-Aminopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (2.3 g.) in methanolic hydrochloric acid (12 ml., containing hydrochloric acid 6 mmol) was stirred at room temperature for one hour. To the resultant solution was added diethyl ether, and the precipitates were collected by filtration and dissolved in a mixture of methanol (50 ml.) and water (10 ml.). The solution was adjusted to pH 3 with an aqueous solution of sodium bicarbonate, treated with activated charcoal (1 g.) and concentrated to a volume of about 20 ml. The precipitating crystals were collected by filtration, washed with water and dried to give 7-[2-(6-aminopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (1.12 g.), mp. 215° to 220° C. (dec.). The mother liquor and washings were combined and concentrated under reduced pressure. The appeared precipitates were collected by filtration, washed with water and dried to give the same object compound (0.36 g.). Total yield 1.48 g.

Workup

  1. filtrationthe precipitates were collected by filtration
  2. dissolutiondissolved in a mixture of methanol (50 ml.) and water (10 ml.)
  3. additiontreated with activated charcoal (1 g.)
  4. concentrationconcentrated to a volume of about 20 ml
  5. filtrationThe precipitating crystals were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-af5c9dd7588b4249ad64831409e476d0
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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