Boron trifluoride etherate → 7-(3-Allylimidazol-2-yl)amino-3-(1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylic acid

HRID 2412473Notes

Reaction equation

HRID 2412473 reaction equation
C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18]3[N:22]([CH2:23][CH:24]=[CH2:25])[CH:21]=[CH:20][N:19]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[SH:27][C:28]1[S:29][CH:30]=[N:31][N:32]=1.B(F)(F)F.CCOCC>C(#N)C>[CH2:23]([N:22]1[CH:21]=[CH:20][N:19]=[C:18]1[NH:17][CH:16]1[C:15](=[O:26])[N:10]2[C:11]([C:12]([OH:14])=[O:13])=[C:6]([CH2:5][S:27][C:28]3[S:29][CH:30]=[N:31][N:32]=3)[CH2:7][S:8][C@H:9]12)[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 704716253-Acetoxymethyl-7-(3-allylimidazol-2-yl)aminoceph-3-em-4-carboxylic acidHCID 178527973HCID 178527973, compound

Product 1

HCID 704722147-(3-Allylimidazol-2-yl)amino-3-(1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylic acidYield 11.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-acetoxymethyl-7-(3-allylimidazol-2-yl)aminoceph-3-em-4-carboxylic acid (0.038 g.) and 2-mercapto-1,3,4-thiadiazole (0.012 g.) in acetonitrile (0.2 ml.) was added boron trifluoride etherate (48% w/w, 32 μl) and the mixture heated at 60° for 2.5 hours. The solvent was evaporated and the residue dissolved in water/MeOH/HOAc 70:30:1 v/v/v (2 ml.). The solution was decanted from the residual tar and then purified by HPLC using water/MeOH/HOAc 70:30:1 then 60:40:1 v/v/v as eluants to give 7-(3-allylimidazol-2-yl)amino-3-(1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylic acid (5 mg.) having the following n.m.r. in d6DMSO+CD3CO2D: 3.20 (d, 2H); 3.50 (d, 1H); 3.75 (d, 1H); 4.31 (d, 1H); 4.60 (d, 1H); 5.0-5.38 (m, 3H); 5.52 (d, 1H); 5.8 (m, 1H); 6.5 (s, 1H); 9.49 (s, 1H).

Workup

  1. temperaturethe mixture heated at 60° for 2.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in water/MeOH/HOAc 70:30:1 v/v/v (2 ml.)
  4. customThe solution was decanted from the residual tar
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-a1319364f1754216b05d75595ae2b473
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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