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Ethyl Acetate → 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[3-(3-formylaminopyridinio)-1-propen-1-yl]-3-cephem-4-carboxylate

HRID 580198
Notes
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Reaction equation

HRID 580198 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:40][O:41][CH3:42])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O:24]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:23])=[C:15]([CH:18]=[CH:19][CH2:20]I)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[CH:43]([NH:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1)=[O:44].C(OCC)(=O)C>CS(C)=O>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:40][O:41][CH3:42])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O-:24])=[O:23])=[C:15]([CH:18]=[CH:19][CH2:20][N+:48]4[CH:49]=[CH:50][CH:51]=[C:46]([NH:45][CH:43]=[O:44])[CH:47]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3815043N-Pyridin-3-yl-formamideHCID 131715581Diphenylmethyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate

Product 1

HCID 1317155867-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[3-(3-formylaminopyridinio)-1-propen-1-yl]-3-cephem-4-carboxylateYield 2.9%

Reagents, catalysts & solvents

1
HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of diphenylmethyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (IX-1) (E, 716 mg, 1 mmole) and 3-formylaminopyridine [prepared according to the procedure of N. Enomoto et al., Bull. Chem. Soc. Japan, 45, 2665 (1972)] (244 mg, 2 mmoles) in DMSO (2 ml) was stirred at room temperature for 1 hour, and poured into ethyl acetate (200 ml). The precipitate was collected by filtration, washed well with ethyl acetate and dried. A mixture of the quaternized salt (500 mg) and sodium bisulfite (50 mg) in HCOOH (5 ml) was stirred at 40°-50° C. for 80 minutes and evaporated to dryness in vacuo. The residue was dissolved in water (40 ml), neutralized with NaHCO3 and then filtered to remove insoluble material. The clear filtrate was chromatographed on a reverse phase column, PrepPAK-500/C18 (100 ml), with water and 5% CH3OH, 10% CH3OH, 20% CH3OH and 30% CH3OH. The fractions containing the desired compound were combined, concentrated in vacuo and lyophilized to give 16 mg (2.9%) of the title compound (I-1F) (E) as a tan powder. Mp. >170° C. (dec.).

Workup

  1. customprepared
  2. filtrationThe precipitate was collected by filtration
  3. washwashed well with ethyl acetate
  4. customdried
  5. additionA mixture of the quaternized salt (500 mg) and sodium bisulfite (50 mg) in HCOOH (5 ml)
  6. customevaporated to dryness in vacuo
  7. dissolutionThe residue was dissolved in water (40 ml)
  8. filtrationfiltered
  9. customto remove insoluble material
  10. customThe clear filtrate was chromatographed on a reverse phase column
  11. additionThe fractions containing the desired compound
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5d44138e06d41af98dd3c0b97fd05ca
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04751295

Reaction notes

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