4-Methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate → p-Methoxybenzyl 7-amino-3-(1,2,3-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

HRID 2253991Notes

Reaction equation

HRID 2253991 reaction equation
[SH:1][C:2]1[S:6][N:5]=[N:4][CH:3]=1.[Na].[NH2:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16]Cl)[CH2:14][S:15][C@H:10]12>CO.C(Cl)Cl>[NH2:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][S:1][C:2]3[S:6][N:5]=[N:4][CH:3]=3)[CH2:14][S:15][C@H:10]12

Participants

5

Reactant 2

HCID 140320224-Methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylateHCID 178527745HCID 178527745, compound

Product 1

HCID 14652933p-Methoxybenzyl 7-amino-3-(1,2,3-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylateYield 71.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium 5-mercapto-1,2,3-thiadiazole (2.45 g) was suspended in methanol (20 ml), and a solution of p-methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate (5.60 g) in methylene chloride (20 ml) was added dropwise. The mixture was stirred for 30 min. under ice-cooling, an insoluble material was filtered off, and the solvent was evaporated to obtain a crude material (6.38 g). The crude material was subjected to silica gel chromatography eluting with chloroform-ethyl acetate to obtain p-methoxybenzyl 7-amino-3-(1,2,3-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate (4.90 g).

Workup

  1. temperaturecooling
  2. filtrationan insoluble material was filtered off
  3. customthe solvent was evaporated
  4. customto obtain a crude material (6.38 g)
  5. washeluting with chloroform-ethyl acetate

Sources & evidence

ORD record
ord-1ef73901760340c98a1aadfb58192c1c
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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