(R)-4-(4-trifluoromethoxy-benzenesulfonyl)-3-(4-trifluoromethoxy-benzylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester → (R)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

HRID 908604Notes

Reaction equation

HRID 908604 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@@H:10]([C:28](=[O:42])[NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=2)[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[F:41][C:38]([F:39])([F:40])[O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][NH:29][C:28]([C@H:10]2[CH2:9][NH:8][CH2:13][CH2:12][N:11]2[S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][CH:18]=2)(=[O:15])=[O:16])=[O:42])=[CH:36][CH:35]=1

Participants

3

Reactant 1

HCID 59703740(R)-4-(4-trifluoromethoxy-benzenesulfonyl)-3-(4-trifluoromethoxy-benzylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59703800(R)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 84.9%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

4N Hydrogen chloride/1,4-dioxane solution (40 ml) was added to the compound (2.20 g) obtained in Step 3, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned by adding chloroform and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium carbonate, filtrated, and concentrated under reduced pressure. The residue was crystallized from a mixed solvent of diisopropyl ether and n-hexane, collected by filtration and dried to give the title compound (1.57 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned
  3. additionby adding chloroform and saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium carbonate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from a mixed solvent of diisopropyl ether and n-hexane
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-ee279c0dc2a84d22b96b21b70bbb5443
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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