Trifluoroacetic acid → HCID 59428405, compound

HRID 503942Notes

Reaction equation

HRID 503942 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][C:32]([O:35]CC4C=CC(OC)=CC=4)=[C:31]([Cl:45])[CH:30]=3)(=[O:28])=[O:27])=[CH:22][C:21]=2[CH3:46])[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[Cl:45][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]([CH3:46])[CH:22]=2)(=[O:28])=[O:27])[CH:34]=[CH:33][C:32]=1[OH:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59428459HCID 59428459, compound

Product 1

HCID 59428405HCID 59428405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid was added to a solution of 3-{4-[3-chloro-4-(4-methoxy-benzyloxy)-benzenesulfonyl]-2-methyl-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared following the procedure described in Example 6) (0.397 g, 0.6939 mmol) in DCM (2 mL). The reaction mixture was stirred at room temperature for 3 hours, and the solvent was then evaporated under reduced pressure. The crude residue was purified via flash chromatography (DCM/MeOH/NH4OH) to give 0.143 g of 2-chloro-4-(3-methyl-4-pyrrolidin-3-yl-benzenesulfonyl)-phenol (white foam) that was transformed in the corresponding hydrochloride salt by addition of a small excess of HCl in 1,4-dioxane. The hydrochloride was recrystallized to afford 0.129 g of a white solid: MP=110.0-112.9° C.

Workup

  1. customprepared
  2. customthe solvent was then evaporated under reduced pressure
  3. customThe crude residue was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-4f50cf31708342078f2d09b2492cc23c
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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