HCID 131711002, compound → HCID 131711001, compound

HRID 462313Notes

Reaction equation

HRID 462313 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:16]([O:18]C(C)(C)C)=[O:17])=[C:6]([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][S:8][C@H:3]12.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)=O>[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][S:8][C@H:3]12

Participants

3

Reactant 1

HCID 131711002HCID 131711002, compound

Product 1

HCID 131711001HCID 131711001, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 175 mg. of tert-butyl 7-amino-3-(2'-ethoxycarbonylvinyl)-3-cephem-4-carboxylate-p-toluenesulfonate in 20 ml. of 98-100 percent formic acid was stirred at room temperature for two hours. The excess formic acid was removed under reduced pressure and the residue was purged once with ethyl acetate and then taken up in ethyl acetate:water mixture. The pH of the mixture was adjusted to 8.0 with saturated sodium bicarbonate solution and the organic layer was separated and removed. The aqueous portion was cooled in an ice bath and the pH was adjusted to 3.5 with 5 percent hydrochloric acid. The precipitate which formed upon acid addition was collected, yielding 67 mg. of the title compound. It had a m.p. of 234°-237° C. (d), and the IR, UV [λmax. 324 mμ (ε = 14,800)] and elemental analysis were consistent with the assigned structure:

Workup

  1. customThe excess formic acid was removed under reduced pressure
  2. customthe residue was purged once with ethyl acetate
  3. customthe organic layer was separated
  4. customremoved
  5. temperatureThe aqueous portion was cooled in an ice bath
  6. customThe precipitate which formed upon acid addition
  7. customwas collected
  8. customyielding 67 mg

Sources & evidence

ORD record
ord-0342c5d5c89347bb8f705c68dcb2aa74
Source dataset
uspto-grants-1977_12
Patent number
US04065620

Reaction notes

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