Hydrochloric Acid → HCID 131712613, compound

HRID 1659846Notes

Reaction equation

HRID 1659846 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:30])[CH:12]([NH:13][C:14](=[O:29])[C:15](=[N:24][O:25][CH2:26][C:27]#[CH:28])[C:16]3[N:17]=[C:18]([NH:21]C=O)[S:19][CH:20]=3)[C@H:4]2[S:3]1.Cl>CO>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:30])[CH:12]([NH:13][C:14](=[O:29])[C:15](=[N:24][O:25][CH2:26][C:27]#[CH:28])[C:16]3[N:17]=[C:18]([NH2:21])[S:19][CH:20]=3)[C@H:4]2[S:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131712612HCID 131712612, compound

Product 1

HCID 131712613HCID 131712613, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-methyl-7-[2-(2-propynyloxyimino)-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (2.1 g) in methanol (42 ml) was added concentrated hydrochloric acid (0.97 ml), and the mixture was stirred for 2 hours at ambient temperature. The methanol was distilled off from the reaction mixture, and the residue was dissolved in water (50 ml) and then filtered. The filtrate was adjusted to pH 3 with a saturated aqueous solution of sodium bicarbonate, and the precipitates were collected by filtration and then dried to give 2-methyl-7-[2-(2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (0.6 g).

Workup

  1. distillationThe methanol was distilled off from the reaction mixture
  2. dissolutionthe residue was dissolved in water (50 ml)
  3. filtrationfiltered
  4. filtrationthe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-37063159bb1d4e4a8f29bd25917aa78c
Source dataset
uspto-grants-1981_12
Patent number
US04305937

Reaction notes

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