p-Toluenesulfonic acid → p-Toluenesulfonic acid

HRID 1463034Notes

Reaction equation

HRID 1463034 reaction equation
[S:1]1[C:5]2([CH2:9][C@@H:8]([C:10]([OH:12])=[O:11])[NH:7][CH2:6]2)[S:4][CH2:3][CH2:2]1.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1.[C:24]1([C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N+]=[N-])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[S:1]1[C:5]2([CH2:9][C@@H:8]([C:10]([O:12][CH:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:11])[NH:7][CH2:6]2)[S:4][CH2:3][CH2:2]1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 128113941,4-Dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, (8S)-

Product 2

HCID 6101p-Toluenesulfonic acidHCID 86739577(S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, p-toluenesulfonate (6.0 g.) in 30 ml. of anhydrous dimethylformamide at 50 ° under argon is added a dimethylformamide solution of diphenyldiazomethane (3.6) portionwise. After 10 minutes at 50°, the solvent is removed under reduced pressure. The residue is dissolved in ethyl acetate and precipitated with ether. The solvent is then decanted and the residue triturated with ethyl acetate/ether to give (S)-1,4-dithia-7-azaspiro [4.4]nonane-8-carboxylic acid, diphenylmethyl ester, p-toluenesulfonate.

Workup

  1. customthe solvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. customprecipitated with ether
  4. customThe solvent is then decanted
  5. customthe residue triturated with ethyl acetate/ether

Sources & evidence

ORD record
ord-0b6fe97c5b3a4b8c9c85d8aa5b7da39f
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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