Trifluoroacetic acid → [(1-{[3-(Propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetic acid

HRID 2390370Notes

Reaction equation

HRID 2390370 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:30]([S:27]([C:23]1[CH:22]=[C:21]([C:20]#[C:19][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][C:9]=2[O:8][CH2:7][C:6]([OH:33])=[O:5])[CH:26]=[CH:25][CH:24]=1)(=[O:29])=[O:28])[CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58521954Tert-butyl[(1-{[3-(propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetate2×

Product 1

HCID 46865201[(1-{[3-(Propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl[(1-{[3-(propylsulfonyl)phenyl]ethynyl}-2-naphthyl)oxy]acetate (Intermediate 218, 60 mg; 0.13 mmol) in DCM (1.2 mL) was treated with trifluoroacetic acid (98 μl; 0.65 mmol). After stirring for 1 hour, the solvents were removed under vacuum to afford a residue, which was purified by preparative HPLC to give the title compound as a beige solid.

Workup

  1. customthe solvents were removed under vacuum
  2. customto afford a residue, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-7648b851b6974f5caee20bb2b7aad6c1
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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