Pyridine → HCID 86738681, compound

HRID 1902506Notes

Reaction equation

HRID 1902506 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.[C:22]1([CH2:28][C:29]([NH:31][CH:32]2[C:48](=[O:49])[N:34]3[CH:35]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[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:48](=[O:49])[N:34]3[CH:35]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])[CH:36]([CH:39]=[O:40])[CH2:37][S:38][C@H:33]23)=[O:30])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 70524350HCID 70524350, compound

Product 1

HCID 86738681HCID 86738681, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

N,N'-Dicyclohexylcarbodiimide (10.8 g.) and pyridine (1.4 g.) were added to a solution of t-butyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (7.1 g.) in dimethylsulfoxide (30 ml.) and benzene (80 ml.). Trifluoroacetic acid (1.0 g.) was added dropwise to the stirred solution at room temperature and stirred overnight. The insoluble substance was filtered off and then ethyl acetate (100 ml.) and water (100 ml.) were added to the filtrate. After filtration, the organic layer was separated and adjusted to pH 3.0, washed with water and saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated in vacuo. The residue was pulverized with petroleum ether to give t-butyl 7-(2-phenylacetamido)-3-formylcepham-4-carboxylate (7.0 g.)

Workup

  1. filtrationThe insoluble substance was filtered off
  2. additionethyl acetate (100 ml.) and water (100 ml.) were added to the filtrate
  3. filtrationAfter filtration
  4. customthe organic layer was separated
  5. washwashed with water and saturated aqueous solution of sodium chloride in turn
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36dad6dd53e5474995ac32aaa16122fc
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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