p-Toluenesulfonic acid → HCID 54254101, compound

HRID 904824Notes

Reaction equation

HRID 904824 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](O)([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:32])(=[O:6])=[O:5])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](=[CH:23][C:24]([OH:26])=[O:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:32])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 204777141-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-tert.-butoxycarbonylmethylbenzyl)benzimidazole

Product 1

HCID 54254101HCID 54254101, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.89 g. of 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-tert.-butoxycarbonylmethylbenzyl)benzimidazole (from Example 6) and 1.2 g. of p-toluenesulfonic acid in 100 ml. of chloroform was heated at reflux for two hours and then cooled to room temperature. The solution was extraced three times with aqueous sodium bicarbonate solution. The aqueous extracts were combined, washed with fresh chloroform and then neutralized to pH 7.0 by the addition of 1 N hydrochloric acid. The acidic solution next was extracted several times with ethyl acetate. The extracts were combined, washed with water and dried. Removal of the solvent by evaporation under reduced pressure provided 1-isopropylsulfonyl-2-amino-6-(α-hydroxycarbonylmethylenebenzyl)benzimidazole.

Workup

  1. temperatureat reflux for two hours
  2. washwashed with fresh chloroform
  3. additionneutralized to pH 7.0 by the addition of 1 N hydrochloric acid
  4. extractionThe acidic solution next was extracted several times with ethyl acetate
  5. washwashed with water
  6. customdried
  7. customRemoval of the solvent
  8. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-55a5d0be66c04f5cabc2f51e6432919b
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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