HCID 57429427, compound → HCID 57429423, compound

HRID 1640015Notes

Reaction equation

HRID 1640015 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[CH:9]=2)[CH2:4][N:3]1[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:28])[C:21]([O:23]C(C)(C)C)=[O:22])=[CH:16][CH:15]=1>C(O)=O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[CH:9]=2)[CH2:4][N:3]1[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:28])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 57429427HCID 57429427, compound

Product 1

HCID 57429423HCID 57429423, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of tert-butyl 2-(4-(1-oxo-6-propylisoindolin-2-yl)phenyl)propanoate (0.084 g, 0.22 mmol) and formic acid (15 mL) was stirred overnight at room temperature. The mixture was then concentrated under reduced pressure, suspended in hexanes (5 mL), sonicated, and the solid collected by filtration to afford 2-(4-(1-oxo-6-propylisoindolin-2-yl)phenyl)propanoic acid (0.041 g, 57%) as a white solid: mp 175-177° C.; 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.6 Hz, 2H), 7.74 (s, 1H), 7.41-7.37 (m, 4H), 4.81 (s, 2H), 3.77 (q, J=7.1 Hz, 1H), 2.70 (t, J=7.4 Hz, 2H), 1.73-1.65 (m, 2H), 1.54 (d, J=7.2 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); ESI MS m/z 324 [M+H]+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customsonicated
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-f59308a3cb5449b1a5f7a1f53692cf10
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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