HCID 131711009, compound → HCID 131711008, compound

HRID 462317Notes

Reaction equation

HRID 462317 reaction equation
C(OC([NH:8][CH:9]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:10]([NH:12][CH:13]1[C:36](=[O:37])[N:15]2[C:16]([C:29]([O:31]C(C)(C)C)=[O:30])=[C:17]([CH:20]=[CH:21][C:22]([O:24]C(C)(C)C)=[O:23])[CH2:18][S:19][C@H:14]12)=[O:11])=O)(C)(C)C>C(O)=O>[NH2:8][CH:9]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:10]([NH:12][CH:13]1[C:36](=[O:37])[N:15]2[C:16]([C:29]([OH:31])=[O:30])=[C:17]([CH:20]=[CH:21][C:22]([OH:24])=[O:23])[CH2:18][S:19][C@H:14]12)=[O:11]

Participants

3

Reactant 1

HCID 131711009HCID 131711009, compound

Product 1

HCID 131711008HCID 131711008, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 25 mg. of tert-butyl 7-(2'-tert-butoxycarbonylamino-2'-phenylacetamido)-3-(2'-tert-butoxycarbonylvinyl)-3-cephem-4-carboxylate, prepared as described in Example 19, in 5 cc of 98-100 percent formic acid was allowed to stand for 1 hour at room temperature. After evaporating under reduced pressure the formic acid, the acid residue was taken up in trifluoroacetic acid and the NMR spectrum was taken. The trifluoroacetic acid was removed under reduced pressure and the acid residue showed a β-lactam in the IR spectrum and an acceptable UV [λ max.=317 mμ (ε = 13,700)]. The bioautograph showed only one antibiotically active zone against Sarcina lutea, which was more polar than cephalexin. Disc plate assay procedures showed antibiotic activity against a variety of Gram positive and Gram negative microorganisms.

Workup

  1. customAfter evaporating under reduced pressure the formic acid
  2. customThe trifluoroacetic acid was removed under reduced pressure

Sources & evidence

ORD record
ord-fdc0860afd134bc9bbcb01429333b6d9
Source dataset
uspto-grants-1977_12
Patent number
US04065620

Reaction notes

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