Hydrochloric Acid → HCID 13472284, compound

HRID 1248029Notes

Reaction equation

HRID 1248029 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:33](=[O:34])[N:12]2[C:13]([C:20]([O:22]CC3C=CC([N+]([O-])=O)=CC=3)=[O:21])=[C:14]([N:17]=[N+:18]=[N-:19])[CH2:15][S:16][C@H:11]12)=[O:8].C1COCC1.Cl>[Zn].O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:33](=[O:34])[N:12]2[C:13]([C:20]([OH:22])=[O:21])=[C:14]([N:17]=[N+:18]=[N-:19])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 13564037HCID 13564037, compound

Product 1

HCID 13472284HCID 13472284, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst3×HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 0.625 g. of p-nitrobenzyl 7β-(2-thienylacetamido)-3-azido-3-cephem-4-carboxylate in 24 ml. of THF was diluted with 10 ml. of cold water and cooled in an ice-water bath. To the cold solution were added portionwise over about two hours 1.58 g. of zinc dust and sufficient 0.1N to 1N hydrochloric acid to maintain the pH of the mixture at about 4.3. Throughout the addition of zinc and acid the temperature of the reaction mixture was maintained at about 5° C. After the zinc dust addition was completed, the pH was adjusted to 2.7 with 1N hydrochloric acid and the mixture filtered. The filtrate was mixed with ethyl acetate and extracted twice with aqueous sodium bicarbonate. The aqueous layer was separated, layered with ethyl acetate, acidified with cold 1N hydrochloric acid, the organic layer separated, washed with brine, dried, and evaporated to yield 0.116 g. of the title acid as a pale yellow solid. The product was triturated with diethyl ether, filtered, and air dried to provide 80 mg. of the product acid as a yellow solid.

Workup

  1. additionTo the cold solution were added portionwise over about two hours 1.58 g
  2. filtrationthe mixture filtered
  3. additionThe filtrate was mixed with ethyl acetate
  4. extractionextracted twice with aqueous sodium bicarbonate
  5. customThe aqueous layer was separated
  6. customthe organic layer separated
  7. washwashed with brine
  8. customdried
  9. customevaporated
  10. customto yield 0.116 g
  11. customThe product was triturated with diethyl ether
  12. filtrationfiltered
  13. customair dried
  14. customto provide 80 mg

Sources & evidence

ORD record
ord-46ff5f7ea7924891a5dd59664f11c6bf
Source dataset
uspto-grants-1985_06
Patent number
US04521598

Reaction notes

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