HCID 13180422, compound → HCID 178494432, compound

HRID 2164985Notes

Reaction equation

HRID 2164985 reaction equation
C([O:5][C:6]([C:8]([O:11]/[N:12]=[C:13](/[C:44]1[N:45]=[C:46]([NH:49]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:47][CH:48]=1)\[C:14]([NH:16][CH:17]1[C:42](=[O:43])[N:19]2[C:20]([C:26]([O:28]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:27])=[C:21]([CH2:24]I)[CH2:22][S:23][C@H:18]12)=[O:15])([CH3:10])[CH3:9])=[O:7])(C)(C)C.[CH3:69][O:70][C:71]1[S:75][CH:74]=[N:73][C:72]=1[CH3:76]>C(Cl)Cl.F[B-](F)(F)F.[Ag+]>[NH2:49][C:46]1[S:47][CH:48]=[C:44](/[C:13](=[N:12]/[O:11][C:8]([C:6]([OH:7])=[O:5])([CH3:9])[CH3:10])/[C:14]([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[C:20]([C:26]([O-:28])=[O:27])=[C:21]([CH2:24][C:74]4[S:75][C:71]([O:70][CH3:69])=[C:72]([CH3:76])[NH+:73]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[N:45]=1

Participants

5

Reactant 2

HCID 13180422HCID 13180422, compoundHCID 20403503HCID 20403503, compound

Product 1

HCID 178494432HCID 178494432, compound

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Procedure

Silver tetrafluoroborate (100 mg, 0.5 mmole) was added to a mixture of diphenylmethyl 7-[(Z)-2-(2-t-butoxycarbonylprop-2-oxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate (VII-4') (577 mg, 0.5 mmole) and 5-methoxy-4-methylthiazole (146 mg, 1 mmole) [prepared according to the procedure described by D. S. Tarbell et al., J. Am. Chem. Soc., 72, 3138 (1950)] in methylene chloride (50 ml). The mixture was stirred for 20 minutes at room temperature and filtered. The filtrate was washed with water, evaporated under reduced pressure and the residue was triturated with ether to give the quaternized salt, which was collected by filtration (yield, 475 mg). The quaternized product was dissolved in cold TFA (2 ml), stirred for 1 hour at room temperature and evaporated under reduced pressure below 30° C., and the residue was triturated with ether. The crude TFA salt was collected by filtration (yield, 281 mg) and purified by HPLC (Column: Lichrosorb RP-18, Solvent: 0.01M NH4H2PO4 (pH 7):CH3OH=85:15). The fractions containing the desired compound were combined and concentrated under reduced pressure below 30° C. The concentrate was acidified to pH 2 (dilute HCl), chromatographed on a column of HP-20 (1.3×10 cm) and eluted with water and then with water-methanol (1:1). The fractions containing the desired product were combined, evaporated under reduced pressure and freeze-dried to give the title compound [Ii] as an amorphous powder. Yield, 61 mg (20%).

Workup

  1. customprepared
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. customevaporated under reduced pressure
  5. customthe residue was triturated with ether
  6. customto give the quaternized salt, which
  7. filtrationwas collected by filtration (yield, 475 mg)
  8. dissolutionThe quaternized product was dissolved in cold TFA (2 ml)
  9. stirringstirred for 1 hour at room temperature
  10. customevaporated under reduced pressure below 30° C.
  11. customthe residue was triturated with ether
  12. filtrationThe crude TFA salt was collected by filtration (yield, 281 mg)
  13. custompurified by HPLC (Column: Lichrosorb RP-18, Solvent: 0.01M NH4H2PO4 (pH 7):CH3OH=85:15)
  14. additionThe fractions containing the desired compound
  15. concentrationconcentrated under reduced pressure below 30° C
  16. customchromatographed on a column of HP-20 (1.3×10 cm)
  17. washeluted with water
  18. additionThe fractions containing the desired product
  19. customevaporated under reduced pressure
  20. customfreeze-dried

Sources & evidence

ORD record
ord-d822e5652db54e76ab3b28c2b9320e4e
Source dataset
uspto-grants-1985_03
Patent number
US04507487

Reaction notes

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