tert-Butyl carbazate → HCID 140338070, compound

HRID 1164424Notes

Reaction equation

HRID 1164424 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C:17](=O)[C:16](=[O:19])[N:6]2[C:7]=1[C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9].[C:20]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:23])[NH:21][NH2:22].Cl.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:25]([O:24][C:20]([NH:21]/[N:22]=[C:17]1/[C@H:5]2[S:4][CH2:3][C:2]([CH3:1])=[C:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16]/1=[O:19])=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 70091tert-Butyl carbazateHCID 10176127Pyridinium chlorideHCID 70464109HCID 70464109, compound

Product 1

HCID 140338070HCID 140338070, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In chloroform (70 ml) are dissolved 2,2,2-trichloroethyl 3-methyl-7-oxo-3-cephem-4-carboxylate (14.30 g), t-butyl carbazate (6.00 g) and pyridine hydrochloride (4.77 g) and the mixture is refluxed in a Dean-Stark trap packed with Molecular Sieve 3A for 30 minutes. The reaction mixture is washed with 1 N-HCl and water in that order, dried over magnesium sulfate and concentrated. The residual oil is subjected to silica gel (240 g) column chromatography and elution is carried out with ethyl acetate-benzene to give crystals of 2,2,2-trichloroethyl (E)-7-t-butoxycarbonylhydrazono-3-methyl-3-cephem-4-carboxylate (4.88 g).

Workup

  1. temperaturethe mixture is refluxed in a Dean-Stark trap
  2. washThe reaction mixture is washed with 1 N-HCl and water in that order
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residual oil is subjected to silica gel (240 g) column chromatography and elution

Sources & evidence

ORD record
ord-c86c08d664ec46f1a49108fa893f1303
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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