Trifluoroacetic acid → HCID 24984018, compound

HRID 503928Notes

Reaction equation

HRID 503928 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([S:35][CH2:36][CH3:37])[CH:30]=3)(=[O:28])=[O:27])=[CH:22][C:21]=2[O:38][CH3:39])[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:36]([S:35][C:31]1[CH:30]=[C:29]([S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH:17]3[CH2:18][CH2:19][NH:15][CH2:16]3)=[C:21]([O:38][CH3:39])[CH:22]=2)(=[O:28])=[O:27])[CH:34]=[CH:33][CH:32]=1)[CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66877113HCID 66877113, compound

Product 1

HCID 24984018HCID 24984018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of 3-[4-(3-ethylsulfanyl-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (60 mg, 0.1256 mmol) in DCM (3 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between NaOH (2 M) and DCM. The organic layer was separated and washed with water, dried over Na2SO4, and evaporated under reduced pressure, affording 3-[4-(3-ethylsulfanyl-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine, which was transformed in the corresponding hydrochloride (white foam, 53 mg) by addition of a small excess of HCl in 1,4-dioxane. MS (M+H)=378.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between NaOH (2 M) and DCM
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9af6529d81c74cc2acb2e380c2c020e6
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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