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

HRID 1473355Notes

Reaction equation

HRID 1473355 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].[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[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-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottom flask was charged with tert-butyl 2-(6-((perfluorophenoxy)sulfonyl)naphthalen-1-yl)pyrrolidine-1-carboxylate (0.315 g, 0.580 mmol) and DCM (3.0 mL) to give a light yellow solution. TFA (1.786 ml, 23.18 mmol) was added in one portion to give a yellow solution. The reaction was stirred for four hours. The reaction was concentrated, dissolved in diethyl ether, and sonicated until a fine white solid triturated out of solution. The solids were filtered, washed with diethyl ether, and vacuum dried overnight to afford perfluorophenyl 5-(pyrrolidin-2-yl)naphthalene-2-sulfonate 2,2,2-trifluoroacetate as an off-white solid. m/z (ESI) 444.0 (M+H)+.

Workup

  1. customto give a light yellow solution
  2. customto give a yellow solution
  3. concentrationThe reaction was concentrated
  4. dissolutiondissolved in diethyl ether
  5. customsonicated until a fine white solid
  6. customtriturated out of solution
  7. filtrationThe solids were filtered
  8. washwashed with diethyl ether, and vacuum
  9. customdried overnight

Sources & evidence

ORD record
ord-6bfe75c8baec4ea8ba4c8c759ee37ca8
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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