p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 614133Notes

Reaction equation

HRID 614133 reaction equation
C1(C([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29]4[N:33]([CH2:34][C:35]5[O:39][CH:38]=[CH:37][CH:36]=5)[N:32]=[N:31][N:30]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1>CC(C)=O>[NH2:20][CH:21]1[C:40](=[O:41])[N:23]2[CH:24]([C:29]3[N:33]([CH2:34][C:35]4[O:39][CH:38]=[CH:37][CH:36]=4)[N:32]=[N:31][N:30]=3)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]12.[CH3:53][C:43]1[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 706050686-(Triphenylmethylamino)-2,2-dimethyl-3-(1-furfuryltetrazol-5-yl)penam

Product 2

HCID 6101p-Toluenesulfonic acidHCID 706048216-Amino-2,2-dimethyl-3-(1-furfuryltetrazol-5-yl)penam

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 0.422 g. (0.75 mmole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-furfuryltetrazol-5-yl)penam in 1 ml. of acetone at ambient temperature, is added 0.142 g. (0.75 mmole) of p-toluenesulfonic acid monohydrate. Stirring is continued for 30 minutes, and then the solvent is removed by evaporation in vacuo. This affords the title compound as its p-toluenesulfonate salt. IR (Nujol mull): 1780 cm-1 (β-lactam). NMR (DMSO-d6): 7.20 ppm (q, 4H), 6.40 ppm (m, 2H), 5.90 ppm (s, 2H), 5.60 ppm (m, 2H), 5.00 ppm (d, 1H), 2.20 ppm (s, 3H), 1.60 ppm (s, 3H), 0.80 ppm (s, 3H).

Workup

  1. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-740eff8b17554794b5d405163242de12
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

Loading…