p-Toluenesulfonic acid monohydrate → HCID 86734859, compound

HRID 1833426Notes

Reaction equation

HRID 1833426 reaction equation
C1(C([NH:20][CH:21]2[C:34](=[O:35])[N:23]3[CH:24]([P:29]([OH:33])([O:31][CH3:32])=[O:30])[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:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43]([OH:46])(=[O:45])=[O:44])=[CH:39][CH:38]=1>CC(C)=O>[C:37]1([CH3:47])[CH:38]=[CH:39][C:40]([S:43]([OH:46])(=[O:44])=[O:45])=[CH:41][CH:42]=1.[NH2:20][CH:21]1[C:34](=[O:35])[N:23]2[CH:24]([P:29]([OH:33])([O:31][CH3:32])=[O:30])[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]12

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86734861HCID 86734861, compound

Product 1

HCID 86734859HCID 86734859, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred slurry of 4.72 g. (0.010 mole) 6-triphenylmethylamino2,2-dimethyl-3-(O-methylphosphono)penam in 50 ml. of dry acetone was added 1.90 g. (0.010 mole) of p-toluenesulfonic acid monohydrate at ambient temperature. The solids dissolved slowly to afford a clear solution. After stirring for about 15 minutes the product started to precipitate. After stirring for about one hour the product was removed by filtration and washed with acetone. 1H-nmr (DMSO-d6) ppm (δ): 1.62 (s,3,CH3), 1.70 (s,3,CH3), 3.62 (d,J = 11,3,OCH3), 3.88 (d,J = 11,1,C-3), 5.05 (m,1,C-6), 5.37 (d,J = 4,1,C-5). IR (Nujol mull): 1765 cm-1 (β-lactam).

Workup

  1. customat ambient temperature
  2. dissolutionThe solids dissolved slowly
  3. customto afford a clear solution
  4. customto precipitate
  5. stirringAfter stirring for about one hour the product
  6. customwas removed by filtration
  7. washwashed with acetone

Sources & evidence

ORD record
ord-19be7fdbfa344ffeb51b0512baefd942
Source dataset
uspto-grants-1978_01
Patent number
US04066657

Reaction notes

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