p-Toluenesulfonic acid monohydrate → HCID 86735718, compound

HRID 372405Notes

Reaction equation

HRID 372405 reaction equation
C([NH:20][CH:21]1[C:42](=[O:43])[N:23]2[CH:24]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[C:25]3([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[S:26][C@H:22]12)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.[C:45]1([CH3:55])[CH:50]=[CH:49][C:48]([S:51]([OH:54])(=[O:53])=[O:52])=[CH:47][CH:46]=1>CC(C)=O>[C:45]1([CH3:55])[CH:46]=[CH:47][C:48]([S:51]([OH:54])(=[O:52])=[O:53])=[CH:49][CH:50]=1.[NH2:20][CH:21]1[C:42](=[O:43])[N:23]2[CH:24]([C:32]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:33])[C:25]3([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[S:26][C@H:22]12

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86735720HCID 86735720, compound

Product 1

HCID 86735718HCID 86735718, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a magnetically stirred solution of 31.4 g. (0.0534 mole) of benzyl 6'-tritylamino-spiro[cyclohexane-1,2'-penam]-3'-carboxylate in 300 ml. of anhydrous acetone, there is added a solution of 10.2 g. (0.0535 mole) of p-toluene-sulfonic acid monohydrate in 300 ml. of anhydrous acetone. After stirring for 2.5 hours at ambient temperature, a precipitate is obtained which is removed by filtration, washed with acetone and then with diethyl ether and dried. 10.1 g. of benzyl 6'-amino-spiro[cyclohexane-1,2'-penam]-3'-carboxylate p-toluenesulfonate are obtained. Yield: 36.5%.

Workup

  1. customa precipitate is obtained which
  2. customis removed by filtration
  3. washwashed with acetone
  4. dry with materialwith diethyl ether and dried

Sources & evidence

ORD record
ord-1c914b1e3102414387fc6bc85d84584e
Source dataset
uspto-grants-1978_05
Patent number
US04091027

Reaction notes

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