p-Toluenesulfonic acid → HCID 86741215, compound

HRID 980327Notes

Reaction equation

HRID 980327 reaction equation
[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](O)([CH2:16][CH2:17][CH2:18][CH2:19][C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([O:28][CH:22]([O:23]5)[O:21]3)[CH2:27]4)[C@H:11]2[N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:9]1=[O:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](=[CH:16][CH2:17][CH2:18][CH2:19][C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([O:28][CH:22]([O:23]5)[O:21]3)[CH2:27]4)[C@H:11]2[N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:9]1=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86741216cis-1,3-dibenzyl-4-hydroxy-4-(4-(2,4,10-trioxaadamantyl)-butyl)-hexahydro-1H-thieno[3,4-d]imidazol-2-one

Product 1

HCID 86741215HCID 86741215, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

910 mg (1.68 mmol) of cis-1,3-dibenzyl-4-hydroxy-4-(4-(2,4,10-trioxaadamantyl)-butyl)-hexahydro-1H-thieno[3,4-d]imidazol-2-one (prepared in accordance with Example 1) are dissolved in 50 ml of toluene and the solution is treated with 20 mg of p-toluenesulphonic acid. The solution is heated to boiling and 20 ml of toluene are distilled off within 1 hour. Thereafter, the solution is evaporated to dryness. The residue remaining is chromatographed on silica gel. Elution with toluene, toluene/ethyl acetate (9:1) and (8:2) gives 839 mg (96% of theory) of cis-1,3-dibenzyl-4-(4-(2,4,10-trioxaadamantyl)-butylidene)-hexahydro-1H-thieno[3,4-d]imidazol-2-one in the form of a light brown oil which solidifies upon drying.

Workup

  1. temperatureThe solution is heated
  2. distillation20 ml of toluene are distilled off within 1 hour
  3. customThereafter, the solution is evaporated to dryness
  4. customThe residue remaining is chromatographed on silica gel
  5. washElution with toluene, toluene/ethyl acetate (9:1) and (8:2)

Sources & evidence

ORD record
ord-e862776c373d44d8a7091c75b1a18282
Source dataset
uspto-grants-1987_01
Patent number
US04636566

Reaction notes

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