Tert-butyl 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoate → 3-(2-(2-(2-(1,3-Dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoic acid
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[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24]>FC(F)(F)C(O)=O>[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[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]Participants
3
Procedure
Into a 10-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoate (intermediate 179.3) (1.5 g, 3.68 mmol, 1.00 equiv) in neat 2,2,2-trifluoroacetic acid (TFA; 2.0 mL). The resulting solution was stirred for 40 min at ambient temperature. Excess TFA was removed under vacuum to afford a pale-yellow oil residue which was purified on a silica gel column eluting with ethyl acetate/petroleum ether (1:5˜1:2˜2:1) to yield 1.1 g (84%) of 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoic acid as a white solid.
Workup
- customInto a 10-mL round-bottom flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- customExcess TFA was removed under vacuum
- customto afford a pale-yellow oil residue which
- customwas purified on a silica gel column
- washeluting with ethyl acetate/petroleum ether (1:5˜1:2˜2:1)
Sources & evidence
- ORD record
- ord-c192640d4e014d3a9d3488f58d0b26d2
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006281B2
Reaction notes
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