p-Toluenesulfonic acid monohydrate → HCID 86734113, compound

HRID 1729669Notes

Reaction equation

HRID 1729669 reaction equation
[Cl:1][C@@:2]1([CH3:35])[C@H:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:9])[N:6]2[C:21](=[O:34])[C@@H:22]([NH:23]C(=O)COC3C=CC=CC=3)[C@H:5]2[S:4][CH2:3]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>CO>[C:37]1([CH3:47])[CH:38]=[CH:39][C:40]([S:43]([OH:46])(=[O:44])=[O:45])=[CH:41][CH:42]=1.[NH2:23][C@@H:22]1[C:21](=[O:34])[N:6]2[C@@H:7]([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)=[O:9])[C@@:2]([Cl:1])([CH3:35])[CH2:3][S:4][C@H:5]12

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68141868HCID 68141868, compound

Product 1

HCID 86734113HCID 86734113, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of p-nitrobenzyl 3β-chloro-3α-methyl-7β-phenoxyacetamidocepham-4α-carboxylate (100 mg) and toluene-p-sulfonic acid monohydrate (75 mg) in methanol (20 ml) is refluxed for 6 hours. The reaction mixture is concentrated to 5 ml, and diluted with ether. The separated crystals are collected by filtration, washed with methanol and ether, and dried to give p-nitrobenzyl 7β-amino-3β-chloro-3α-methylcepham-4α-carboxylate p-toluenesulfonic acid salt. (78 mg).

Workup

  1. concentrationThe reaction mixture is concentrated to 5 ml
  2. additiondiluted with ether
  3. filtrationThe separated crystals are collected by filtration
  4. washwashed with methanol and ether
  5. customdried

Sources & evidence

ORD record
ord-04f39c27a6db40808a00d0bd1e129b65
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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