1,4-Dioxane hydrochloride → (R)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

HRID 908645Notes

Reaction equation

HRID 908645 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C@@H:17]([C:33](=[O:47])[NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][C:43]([F:46])([F:45])[F:44])=[CH:38][CH:37]=2)[CH2:16]1)=O)(C)(C)C>>[F:46][C:43]([F:44])([F:45])[O:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:33]([C@H:17]2[CH2:16][NH:15][CH2:20][CH2:19][N:18]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:31][CH2:32]3)=[CH:26][CH:25]=2)(=[O:22])=[O:23])=[O:47])=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59703777(R)-4-(4-cyclopropyl-benzenesulfonyl)-3-(4-trifluoromethoxy-benzylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59703776(R)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 81.7%

Procedure

4N Hydrogen chloride/1,4-dioxane solution (1.3 ml) was added to the compound (130 mg) obtained in Step 3, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned by adding ethyl acetate, saturated aqueous sodium hydrogen carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (chloroform:methanol=9:1) to give the title compound (88 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned
  3. additionby adding ethyl acetate, saturated aqueous sodium hydrogen carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by thin layer silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-c70719f795824ee5b136ab1f2016527c
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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