Trifluoroacetic acid → 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylic acid

HRID 464221Notes

Reaction equation

HRID 464221 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:13][N:12]=[C:11]([C:14](=[N:51][O:52][CH2:53][CH3:54])[C:15]([NH:17][CH:18]2[C:49](=[O:50])[N:20]3[C:21]([C:33]([O:35]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:34])=[C:22]([CH:25]=[CH:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:13][N:12]=[C:11]([C:14](=[N:51][O:52][CH2:53][CH3:54])[C:15]([NH:17][CH:18]2[C:49](=[O:50])[N:20]3[C:21]([C:33]([OH:35])=[O:34])=[C:22]([CH:25]=[CH:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131714369Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate

Product 1

HCID 1317143707-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylic acidYield 53.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (1.2 ml) was added to a suspension of benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (cis-trans mixture) (1.0 g) in dichloromethane (10 ml) and anisole (0.65 ml) at ambient temperature and stirred for 2 hours at the same temperature. To the resulting solution was added isopropyl ether (50 ml) and stirred. The precipitates, collected by filtration, were washed with diisopropyl ether. The precipitates were added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with 20% aqueous potassium carbonate. The separated aqueous layer was adjusted to pH 3.5 with 10% hydrochloric acid under ice-cooling. The resulting precipitates were filtered off, washed with ice water and dried over phosphorus pentoxide in vacuo to give 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylic acid (syn isomer) (cis-trans mixture) (0.4 g).

Workup

  1. stirringstirred
  2. filtrationThe precipitates, collected by filtration
  3. washwere washed with diisopropyl ether
  4. additionThe precipitates were added to a mixture of ethyl acetate and water
  5. temperaturecooling
  6. customThe resulting precipitates
  7. filtrationwere filtered off
  8. washwashed with ice water
  9. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-7b73db3c192a40629a4e71388ba3707c
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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