p-Toluenesulfonic acid monohydrate → HCID 70604552, compound

HRID 614134Notes

Reaction equation

HRID 614134 reaction equation
C1(C([NH:20][CH:21]2[C:41](=[O:42])[N:23]3[CH:24]([C:29]4[N:33]([CH2:34][C:35]5[O:39][C:38]([CH3:40])=[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.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[NH2:20][CH:21]1[C:41](=[O:42])[N:23]2[CH:24]([C:29]3[N:33]([CH2:34][C:35]4[O:39][C:38]([CH3:40])=[CH:37][CH:36]=4)[N:32]=[N:31][N:30]=3)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]12

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 70604632HCID 70604632, compound

Product 1

HCID 70604552HCID 70604552, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 1.827 g. of 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[5-methylfurfuryl]tetrazol-5-yl)penam in 3 ml. of acetone is added a solution of 0.59 g. of p-toluenesulfonic acid monohydrate in 2 ml. of acetone. The mixture is stirred at ambient temperature for 30 minutes, and then the precipitate which has formed is filtered off. This affords 0.87 g. (54% yield) of the title compound as its p-toluenesulfonate salt. The NMR spectrum of the product (CDCl3) shows absorptions at 7.28 ppm (q, 4H), 6.50 ppm (d, 1H), 6.01 ppm (s, 1H), 5.86 ppm (s, 2H), 5.71 ppm (s, 1H), 5.68 ppm (d, 1H), 5.09 ppm (d, 1H), 2.00 ppm (2s, 6H), 1.66 ppm (s, 3H) and 0.88 ppm (s, 3H).

Workup

  1. customthe precipitate which has formed
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-94972eb16f704b11ab2caab573aa64ba
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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