Anisole → HCID 13938971, compound

HRID 1681453Notes

Reaction equation

HRID 1681453 reaction equation
[NH2:1][CH:2]1[C:28](=[O:29])[N:4]2[C:5]([C:12]([O:14]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:13])=[C:6](/[CH:9]=[CH:10]\[CH3:11])[CH2:7][S:8][C@H:3]12.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:1][CH:2]1[C:28](=[O:29])[N:4]2[C:5]([C:12]([OH:14])=[O:13])=[C:6](/[CH:9]=[CH:10]\[CH3:11])[CH2:7][S:8][C@H:3]12

Participants

4

Reactant 2

HCID 7519AnisoleHCID 67899263HCID 67899263, compound

Product 1

HCID 13938971HCID 13938971, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

54.5 g (0.123 mol of benzhydryl 7-amino-3-[(Z)-1-propen-1-yl]-3-cephem-4-carboxylate (Example 10) are added to a stirred solution of 500 ml of trifluoroacetic acid (TFA) and 31 ml of anisole, which is cooled to 0° C. The mixture is stirred at room temperature for 1 hour and is then concentrated in vacuo at 30° C. and the oily residue is stirred with 600 ml of ether for 1 hour. The precipitate is filtered off with suction and washed with 300 to 400 ml of ether and the residue on the filter is dried in vacuo for 3 hours. The trifluoroacetate is suspended in 300 ml of water, the suspension is cooled to +5° C. and the pH is brought to 0.2-0.4 with 12N HCl. The resulting clear solution is cooled to +5° C. and stirred with 4 g of active charcoal for 10 minutes. The active charcoal is filtered off with suction over kieselguhr and rinsed with about 50 ml of 0.1N HCl. The filtrate is brought to pH 2.1 at +5° C. with 20% strength NaOH and the product which has precipitated out is left to stand in a refrigerator for 1 hour in order to bring the crystallization to completion. The crystal sludge is filtered off with suction, washed with 100 ml of water and 300 ml of acetone and dried in vacuo.

Workup

  1. concentrationis then concentrated in vacuo at 30° C.
  2. stirringthe oily residue is stirred with 600 ml of ether for 1 hour
  3. filtrationThe precipitate is filtered off with suction
  4. washwashed with 300 to 400 ml of ether
  5. customthe residue on the filter is dried in vacuo for 3 hours
  6. temperaturethe suspension is cooled to +5° C.
  7. temperatureThe resulting clear solution is cooled to +5° C.
  8. stirringstirred with 4 g of active charcoal for 10 minutes
  9. filtrationThe active charcoal is filtered off with suction over kieselguhr
  10. washrinsed with about 50 ml of 0.1N HCl
  11. customis brought to pH 2.1 at +5° C. with 20% strength NaOH
  12. customthe product which has precipitated out
  13. waitis left
  14. waitto stand in a refrigerator for 1 hour in order
  15. customthe crystallization to completion
  16. filtrationThe crystal sludge is filtered off with suction
  17. washwashed with 100 ml of water and 300 ml of acetone
  18. customdried in vacuo

Sources & evidence

ORD record
ord-19c156a5f95c4fadb4c32dbad60e4aaf
Source dataset
uspto-grants-1992_12
Patent number
US05171854

Reaction notes

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