Hydrochloric Acid → HCID 88469363, compound

HRID 905443Notes

Reaction equation

HRID 905443 reaction equation
C([NH:3][C:4]1[S:5][C:6]([CH2:9][C:10]([NH:12][CH:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])=[CH:7][N:8]=1)=O.Cl>CO.O1CCCC1.C(=O)(O)[O-].[Na+]>[NH2:3][C:4]1[S:5][C:6]([CH2:9][C:10]([NH:12][CH:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])=[CH:7][N:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 88469656HCID 88469656, compound

Product 1

HCID 88469363HCID 88469363, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 7-[2-(2-formamidothiazol-5-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylic acid (4.67 g) and conc. hydrochloric acid (4.67 g) in methanol (93 ml) and tetrahydrofuran (46 ml) was stirred at 30° C. for 4 hours. After the organic solvent was removed by evaporation, to the residue was added water (70 ml), followed by adjusting to pH 6 to 7 with 10% aqueous solution of sodium hydroxide. After the insoluble substance was removed by filtration, the filtrate was adjusted to pH 3.0 with 10% hydrochloric acid under cooling, followed by stirring at the same temperature for 20 minutes. The precipitated substance was collected by filtration, washed with water and dried to give a residue, which was dissolved in an aqueous solution of sodium bicarbonate and then chromatographed on alumina (12 ml) using 5% aqueous sodium acetate as an eluent. The fractions containing the desired compound were collected and acidified to pH 3.1 with 10% hydrochloric acid, and the precipitated substance was collected by filtration and then dried to give 7-[2-(2-aminothiazol-5-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (1.52 g), mp>290° C.

Workup

  1. customAfter the organic solvent was removed by evaporation, to the residue
  2. additionwas added water (70 ml)
  3. customAfter the insoluble substance was removed by filtration
  4. temperatureunder cooling
  5. stirringby stirring at the same temperature for 20 minutes
  6. filtrationThe precipitated substance was collected by filtration
  7. washwashed with water
  8. customdried
  9. customto give a residue, which
  10. customchromatographed on alumina (12 ml)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. filtrationthe precipitated substance was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-df1ef404743340bb943b33d1304ec3f6
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

Loading…