HCID 131711006, compound → HCID 131711005, compound

HRID 462315Notes

Reaction equation

HRID 462315 reaction equation
[C:1]([CH:3]=[CH:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:31])[N:9]2[C:10]=1[C:11]([O:13]C(C)(C)C)=[O:12])#[N:2]>C(O)=O>[C:1]([CH:3]=[CH:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18](=[O:31])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])#[N:2]

Participants

3

Reactant 1

HCID 131711006HCID 131711006, compound

Product 1

HCID 131711005HCID 131711005, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Each of the cis-and trans-isomers of tert-butyl 3-(2'-cyanovinyl)-7-phenoxyacetamido-3-cephem-4-carboxylate from Example 17 was in turn treated with 98-100 percent formic acid for 1 hour at room temperature to cleave the tert-butyl ester groups therefrom. After evaporation under reduced pressure of the excess formic acid, the acid residue was separated as an oil. Each product [the cis-or trans-isomer of the titled compound] showed a large antibiotic activity zone at 1 microgram/milliliter on a bioautograph test against B. subtilis.

Workup

  1. customAfter evaporation under reduced pressure of the excess formic acid
  2. customthe acid residue was separated as an oil

Sources & evidence

ORD record
ord-0ca60ff45d90461a9911be71d9fd5408
Source dataset
uspto-grants-1977_12
Patent number
US04065620

Reaction notes

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