Trifluoroacetic acid → Perfluorophenyl 5-(pyrrolidin-2-yl)naphthalene-2-sulfonate 2,2,2-trifluoroacetate

HRID 1473349Notes

Reaction equation

HRID 1473349 reaction equation
[F:1][C:2]1[C:33]([F:34])=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:3]=1[O:4][S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1C(OC(C)(C)C)=O)=[CH:13][CH:12]=[CH:11]2)(=[O:7])=[O:6].[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>C(Cl)Cl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[NH:19]1[CH2:20][CH2:21][CH2:22][CH:18]1[C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[CH:17][C:8]([S:5]([O:4][C:3]1[C:30]([F:37])=[C:31]([F:36])[C:32]([F:35])=[C:33]([F:34])[C:2]=1[F:1])(=[O:7])=[O:6])=[CH:9]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687397Tert-butyl 2-(6-((perfluorophenoxy)sulfonyl)naphthalen-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86687398Perfluorophenyl 5-(pyrrolidin-2-yl)naphthalene-2-sulfonate 2,2,2-trifluoroacetateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25-mL round-bottom flask was charged with tert-butyl 2-(6-((perfluorophenoxy)sulfonyl)naphthalen-1-yl)pyrrolidine-1-carboxylate (674 mg, 1.240 mmol), DCM (4960 μl), and trifluoroacetic acid (2389 μl, 31.0 mmol) to give a clear, very lightly-colored solution After 1 h, the mixture was concentrated, and the residue was taken up in diethyl ether and sonicated, resulting in the formation of a white solid. The mixture was filtered, and the collected solid was washed with diethyl ether, dried over a stream of N2 (g) for 20 min, then dried under vacuum for 30 min to give perfluorophenyl 5-(pyrrolidin-2-yl)naphthalene-2-sulfonate 2,2,2-trifluoroacetate (647 mg, 1.161 mmol, 94% yield) as a white solid: m/z (ESI) 444.2 (M+H)+.

Workup

  1. customto give a clear, very lightly-colored solution After 1 h
  2. concentrationthe mixture was concentrated
  3. customsonicated
  4. customresulting in the formation of a white solid
  5. filtrationThe mixture was filtered
  6. washthe collected solid was washed with diethyl ether
  7. dry with materialdried over a stream of N2 (g) for 20 min
  8. customdried under vacuum for 30 min

Sources & evidence

ORD record
ord-9826dd0a52f64ab3a8d8703c521c5f05
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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