HCID 131713046, compound → HCID 131713045, compound

HRID 1982673Notes

Reaction equation

HRID 1982673 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([NH:44]C=O)[N:39]=1)[C:7]([NH:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:33]([OH:35])=[O:34])=[C:14]([CH2:17][S:18][C:19]3[S:20][C:21]([CH2:24][NH:25]C(OC(C)(C)C)=O)=[N:22][N:23]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3]>C(O)=O>[CH2:1]([O:4][N:5]=[C:6]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([NH2:44])[N:39]=1)[C:7]([NH:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:33]([OH:35])=[O:34])=[C:14]([CH2:17][S:18][C:19]3[S:20][C:21]([CH2:24][NH2:25])=[N:22][N:23]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 131713046HCID 131713046, compound

Product 1

HCID 131713045HCID 131713045, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 7-[2-allyloxyimino-2-(6-formamidopyridin-2-yl)acetamido]-3-(5-tert-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (2.7 g) in formic acid (27 ml) was stirred for 2 hours at ambient temperature and evaporated to dryness. To the residue were added methanol (50 ml) and concentrated hydrochloric acid (0.82 g), and the mixture was stirred for an hour at ambient temperature. The solvent was evaporated and the residue was dissolved in water (50 ml), adjusted to pH 4 to 5 with an aqueous solution of sodium bicarbonate, treated with an activated charcoal and then subjected to column chromatography over nonionic adsorption resin, "Diaion HP 20" (80 ml). The column was washed with water and eluted with 50% aqueous methanol. The eluent containing a desired compound was evaporated to remove the methanol and then lyophilized to give 7-[2-allyloxyimino-2-(6-aminopyridin-2-yl)acetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (0.6 g), mp 180° C. (dec.).

Workup

  1. customevaporated to dryness
  2. additionTo the residue were added methanol (50 ml) and concentrated hydrochloric acid (0.82 g)
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in water (50 ml)
  5. additiontreated with an activated charcoal
  6. washThe column was washed with water
  7. washeluted with 50% aqueous methanol
  8. additionThe eluent containing a desired compound
  9. customwas evaporated
  10. customto remove the methanol

Sources & evidence

ORD record
ord-5363539866454496992928ca41eef932
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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