HCID 86735542, compound → HCID 131711053, compound

HRID 1679189Notes

Reaction equation

HRID 1679189 reaction equation
[N:1]([CH:4]1[C:34](=[O:35])[N:6]2[CH:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:8]([CH2:16][O:17][C:18](=[O:20])[CH3:19])(OS(C)(=O)=O)[CH2:9][S:10][C@:5]12[S:36][CH3:37])=[N+:2]=[N-:3]>CCOC(C)=O>[N:1]([CH:4]1[C:34](=[O:35])[N:6]2[C:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])=[C:8]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:9][S:10][C@:5]12[S:36][CH3:37])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 86735542HCID 86735542, compound

Product 1

HCID 131711053HCID 131711053, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-nitrobenzyl 7-azido-6-methylthio-3-acetoxymethyl-3-methylsulfonyloxy-cepham-4-carboxylate (20 mg.) and EM silica gel 60 (500 mg.) in 3:1 φH-EtOAc (1 ml.) is stirred at room temperature for 4 hours. The mixture is diluted with EtOAc (3 ml.) and filtered through a small sintered glass funnel containing a pad of MgSO4. The silica gel is washed with more EtOAc (2 × 2 ml.). Evaporation of the filtrate in vacuo provides a 3:7 mixture (19 mg.) of starting material and p-nitrobenzyl 7-azido-6-methylthio-3-acetoxymethyl-ceph-3-em-4-carboxylate.

Workup

  1. filtrationfiltered through a small sintered glass funnel
  2. additioncontaining a pad of MgSO4
  3. washThe silica gel is washed with more EtOAc (2 × 2 ml.)
  4. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-036025580b9f4d16a899716ef086048c
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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