Trifluoroacetic acid → 4-(1,3-Dioxoisoindolin-2-yl)-4-(ethoxycarbonyl)-4-fluorobutanoic acid

HRID 618703Notes

Reaction equation

HRID 618703 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]([F:27])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16].FC(F)(F)C(O)=O>C(Cl)Cl>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([F:27])[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54501069Tert-butyl 4-(1,3-dioxoisoindolin-2-yl)-4-fluoro-4-ethoxycarbonylbutanoate

Product 1

HCID 218479184-(1,3-Dioxoisoindolin-2-yl)-4-(ethoxycarbonyl)-4-fluorobutanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 4-(1,3-dioxoisoindolin-2-yl)-4-fluoro-4-ethoxycarbonylbutanoate (1.1 g, 3 mmol) and trifluoroacetic acid (5 mL) in methylene chloride (5 mL) is stirred for 18 hours and then with methylene chloride (50 mL) for 10 min. The organic layer is washed with water and brine (30 mL each), and dried over sodium sulfate. The solvent is removed in vacuo to yield 4-(1,3-dioxoisoindolin-2-yl)-4-(ethoxycarbonyl)-4-fluorobutanoic acid which can be purified by chromatography or used in the next step without further purification.

Workup

  1. washThe organic layer is washed with water and brine (30 mL each)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c1416dc3169d4a96abee300c3aee9b75
Source dataset
uspto-grants-1999_09
Patent number
US05955476

Reaction notes

Loading…