Methanol → Diphenylmethyl 7-amino-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate

HRID 2210970Notes

Reaction equation

HRID 2210970 reaction equation
C1(CC([NH:10][CH:11]2[C:43](=[O:44])[N:13]3[C:14]([C:27]([O:29][CH:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[S:28])=[C:15]([C:18]4[S:19][C:20]5[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=5[N:22]=4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>C(Cl)Cl>[NH2:10][CH:11]1[C:43](=[O:44])[N:13]2[C:14]([C:27]([O:29][CH:30]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[S:28])=[C:15]([C:18]3[S:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:16][S:17][C@H:12]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 131719159Diphenylmethyl 7-phenylacetamido-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate

Product 1

HCID 131719158Diphenylmethyl 7-amino-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

557 mg of diphenylmethyl 7-phenylacetamido-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate were dissolved in 6 ml of methylene chloride, and the resulting solution was then cooled to -15° C. Afterward, to the cooled solution were added 0.16 ml of pyridine and 268 mg of phosphorus pentachloride, followed by stirring the resultant mixture at -5° C. for 1 hour and 30 minutes. Next, the mixture was cooled to -20° C., and 2.1 ml of methanol were then added thereto. The resulting solution was stirred again at -5° C. for 3 hours to continue the reaction (for the removal of the 7-phenylacetyl group). Thereafter, 6 ml of water were added to the reaction solution which was then further stirred at the same temperature for 1 hour, followed by separation into the aqueous and organic layers. 6 ml of water were added to the resultant organic layer which was then adjusted to pH 7 with an aqueous saturated solution of sodium hydrogen carbonate. After separation from the aqueous layer, the collected organic layer was dried over anhydrous magnesium sulfate. The dried organic solution obtained was distilled under reduced pressure to remove the solvent therefrom, and the resultant residue was then purified by a column chromatography on 35 g of silica gel (as developed with mixed solvents of toluene and ethyl acetate at ratio of 1:1 by volume) to give diphenylmethyl 7-amino-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate as white crystals.

Workup

  1. custom30 minutes
  2. temperatureNext, the mixture was cooled to -20° C.
  3. customthe reaction (
  4. customfor the removal of the 7-phenylacetyl group)
  5. additionThereafter, 6 ml of water were added to the reaction solution which
  6. stirringwas then further stirred at the same temperature for 1 hour
  7. customfollowed by separation into the aqueous and organic layers
  8. addition6 ml of water were added to the resultant organic layer which
  9. customAfter separation from the aqueous layer
  10. dry with materialthe collected organic layer was dried over anhydrous magnesium sulfate
  11. customThe dried organic solution obtained
  12. distillationwas distilled under reduced pressure
  13. customto remove the solvent
  14. customthe resultant residue was then purified by a column chromatography on 35 g of silica gel (as developed with mixed solvents of toluene and ethyl acetate at ratio of 1:1 by volume)

Sources & evidence

ORD record
ord-8aa06c323acb47bdbe8dec0b3bd6bb6a
Source dataset
uspto-grants-1995_10
Patent number
US05461044

Reaction notes

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