Pyridine → HCID 86738682, compound

HRID 1902510Notes

Reaction equation

HRID 1902510 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.[C:22]1([CH2:28][C:29]([NH:31][CH:32]2[C:57](=[O:58])[N:34]3[CH:35]([C:41]([O:43][CH:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])[CH:36]([CH2:39][OH:40])[CH2:37][S:38][C@H:33]23)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.FC(F)(F)C(O)=O>CS(C)=O.C1C=CC=CC=1>[C:22]1([CH2:28][C:29]([NH:31][CH:32]2[C:57](=[O:58])[N:34]3[CH:35]([C:41]([O:43][CH:44]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)=[O:42])[CH:36]([CH:39]=[O:40])[CH2:37][S:38][C@H:33]23)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 70524691HCID 70524691, compound

Product 1

HCID 86738682HCID 86738682, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

Dicyclohexylcarbodiimide (1.8 g.) and pyridine (0.23 g.) were added to a solution of diphenylmethyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (1.5 g.) in dimethylsulfoxide (7 ml.) and benzene (15 ml.). To the solution was added trifluoroacetic acid (0.17 g.) and the mixture was stirred at room temperature overnight. After filtration, the filtrate was poured in a mixture of ethyl acetate (100 ml.) and water (100 ml.). The solution was adjusted to pH 3.0, and the ethyl acetate layer was separated, washed with aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The insoluble substance was removed by filtration and the filtrate was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and methylene chloride. The eluate was concentrated in vacuo to give diphenylmethyl 7-(2-phenylacetamido)-3-formylcepham-4-carboxylate (0.6 g.).

Workup

  1. filtrationAfter filtration
  2. additionthe filtrate was poured in a mixture of ethyl acetate (100 ml.) and water (100 ml.)
  3. customthe ethyl acetate layer was separated
  4. washwashed with aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe insoluble substance was removed by filtration
  8. washeluted with a mixture of ethyl acetate and methylene chloride
  9. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-6bfa4162d46c4c1898e072f578248fe8
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

Loading…