Pyridine → HCID 88793624, compound

HRID 1576803Notes

Reaction equation

HRID 1576803 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][C:9]1[CH:14]([C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[N:13]2[C:31](=[O:42])[C@@H:32]([NH:33][C:34](=[O:41])[CH2:35][C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[C@H:12]2[S:11][CH:10]=1>[O-2].[O-2].[O-2].[Cr+6].C(Cl)Cl>[CH:8]([C:9]1[CH:14]([C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[N:13]2[C:31](=[O:42])[C@@H:32]([NH:33][C:34](=[O:41])[CH2:35][C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[C@H:12]2[S:11][CH:10]=1)=[O:7]

Participants

5

Reactant 2

HCID 1049PyridineHCID 15742497HCID 15742497, compound

Product 1

HCID 88793624HCID 88793624, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In this preparation 31 g. of dried chromium trioxide is added to a mixture of 51 g. of dry pyridine and 800 ml. of dry methylene chloride and stirred at 15°C under nitrogen for 20 minutes. 26 Grams of benzhydryl 3-hydroxymethyl-7β-(thiophen-2-yl-acetamido)-ceph-2-em-4carboxylate in 250 ml. of dry methylene chloride is added in one portion. The resulting mixture is stirred for 30 minutes and then filtered through diatomaceous earth. The contents of the reaction flask and the diatomaceous earth are washed with 500 ml. of methylene chloride and combined with the preceding filtrate and then washed with 400 ml. of 5% aqueous potassium hydroxide solution, 500 ml. of 20% aqueous hydrochloric acid and twice with 400 ml. brine. The aqueous washings are back extracted with 500 ml. of methylene chloride and the extracts added to the previously washed methylene chloride filtrate, then dried over sodium sulfate and then stirred for one hour with 30 g. of silica gel. The mixture is filtered and the silica gel washed with 400 ml. 1:1 vol. ethyl acetate/methylene chloride. The combined filtrates are evaporated to dryness under reduced pressure and the resulting residue (26 g.) is recrystallized from ethyl ether/methylene chloride affording 21.4 g. of benzhydryl 3-formyl-7β-(thiophen-2-yl-acetamido)-ceph-2-em-4-carboxylate.

Workup

  1. customIn this preparation 31 g
  2. filtrationfiltered through diatomaceous earth
  3. washThe contents of the reaction flask and the diatomaceous earth are washed with 500 ml
  4. washwashed with 400 ml
  5. extractionThe aqueous washings are back extracted with 500 ml
  6. additionof methylene chloride and the extracts added to the previously washed methylene chloride filtrate
  7. dry with materialdried over sodium sulfate
  8. stirringstirred for one hour with 30 g
  9. filtrationThe mixture is filtered
  10. washthe silica gel washed with 400 ml
  11. customThe combined filtrates are evaporated to dryness under reduced pressure
  12. customthe resulting residue (26 g.) is recrystallized from ethyl ether/methylene chloride affording 21.4 g

Sources & evidence

ORD record
ord-24d2d1daef6847048c7eea149a95a724
Source dataset
uspto-grants-1976_09
Patent number
US03983113

Reaction notes

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