p-Toluenesulfonic acid → HCID 131709915, compound

HRID 1580486Notes

Reaction equation

HRID 1580486 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH2:21][C:22]1[CH:27]([C:28]([OH:30])=[O:29])[N:26]2[C:31](=[O:43])[CH:32]([NH:33][C:34](=[O:42])[CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:25]2[S:24][CH:23]=1>O1CCOCC1>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([CH2:21][C:22]2[CH:27]([C:28]([OH:30])=[O:29])[N:26]3[C:31](=[O:43])[CH:32]([NH:33][C:34](=[O:42])[CH2:35][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C@H:25]3[S:24][CH:23]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7519AnisoleHCID 70524001HCID 70524001, compound

Product 1

HCID 131709915HCID 131709915, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.044 g of anisole and 0.0172 g of p-toluenesulphonic acid in 2 ml of anhydrous dioxane is mixed with 0.035 g of 3-hydroxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid and the resulting solution is left to stand for one hour at room temperature. The solvent is removed under reduced pressure and the residue is triturated with diethyl ether to remove the excess of p-toluenesulphonic acid and is worked up in accordance with the process described in example 6. 3-(4-Methoxy-benzyl)-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid containing a small amount of the corresponding 2-methoxybenzyl compound is thus obtained; in a thin layer chromatogram, this acid does not differ from the product of the process of example 1.

Workup

  1. waitthe resulting solution is left
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is triturated with diethyl ether
  4. customto remove the excess of p-toluenesulphonic acid

Sources & evidence

ORD record
ord-843501dac3aa4d3ca68e96fa74581f6c
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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