p-Toluenesulfonic acid monohydrate → HCID 131715885, compound

HRID 1194161Notes

Reaction equation

HRID 1194161 reaction equation
C([NH:20][C@@H:21]1[C:48](=[O:49])[N:23]2[C:24]([C:32]([O:34][CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[S:33])=[C:25]([CH2:28][C:29](=[O:31])[NH2:30])[CH2:26][S:27][C@H:22]12)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.[C:51]1([CH3:61])[CH:56]=[CH:55][C:54]([S:57]([OH:60])(=[O:59])=[O:58])=[CH:53][CH:52]=1>C(OCC)(=O)C>[C:51]1([CH3:61])[CH:52]=[CH:53][C:54]([S:57]([OH:60])(=[O:58])=[O:59])=[CH:55][CH:56]=1.[CH:35]([O:34][C:32]([C:24]1[N:23]2[C:48](=[O:49])[C@@H:21]([NH2:20])[C@H:22]2[S:27][CH2:26][C:25]=1[CH2:28][C:29](=[O:31])[NH2:30])=[S:33])([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131715884HCID 131715884, compound

Product 1

HCID 131715885HCID 131715885, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.56 g (0.8 mM) of benzhydryl 7β-tritylamino-3-carbamoylmethylthio-3-cephem-4-carboxylate obtained in Example 2(a) in 10 ml of ethyl acetate, 0.18 g (0.96 mM) of p-toluenesulfonic acid monohydrate was added under ice-cooling, and the mixture was stirred for 4 hours. After the reaction, the white crystals which formed were collected by filtration to give 0.392 g of 7β-amino-3-carbamoylmethylthio-3-cephem-4-carboxylic acid benzhydryl ester p-toluenesulfonate.

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. customthe white crystals which formed
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-336896841ff346529974a8bff6783d8f
Source dataset
uspto-grants-1989_03
Patent number
US04812562

Reaction notes

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