Hydrochloric Acid → HCID 88656749, compound

HRID 1164562Notes

Reaction equation

HRID 1164562 reaction equation
Cl.C([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[O:26])[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])[N:9]=1)=O>CO>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[O:26])[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])[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 88736241HCID 88736241, compound

Product 1

HCID 88656749HCID 88656749, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of conc.hydrochloric acid (2.44 g) and methanol (10 ml) was added to a mixture of 7-[2-(2-formamido-4-thiazolyl)glyoxyloylamino]-3-cephem-4-carboxylic acid (2.44 g) in methanol (40 ml) under ice-cooling, stirred at 20° to 22° C. for 5 hours and filtered. The filtrate was concentrated under reduced pressure, and water (100 ml) was added to the residue adjusted to pH 6.5 with sodium bicarbonate with stirring and filtered. The filtrate was washed with ethyl acetate, and adjusted to pH 3.5 with 10% hydrochloric acid. The resultant precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-amino-4-thiazolyl)glyoxyloylamino]-3-cephem-4-carboxylic acid (0.492 g). The filtrate and washings were subjected to column chromatography on macroporous, non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.), washed with water and eluted with 15% isopropyl alcohol. The isopropyl alcohol was distilled off under reduced pressure and the remaining solution was lyophilized to give the same object compound (1.561 g). Total yield 2.053 g.

Workup

  1. additionA mixture of conc
  2. temperaturecooling
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure, and water (100 ml)
  5. additionwas added to the residue
  6. stirringwith stirring
  7. filtrationfiltered
  8. washThe filtrate was washed with ethyl acetate
  9. customThe resultant precipitates
  10. filtrationwere collected by filtration
  11. washwashed with water
  12. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-3a50d102b34b4a308aabb292ad6e1de2
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

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