Dicyclohexylcarbodiimide → Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

To a solution of chroman (compound 5) (5.0 g, 13.8 mmole) in dichloromethane (30 ml), compound 7 (3.5 g, 16 mmole) and N-hydroxysuccinimide (1.8 g, 16 mmole) were added, as shown in FIG. 7. The mixture was stirred at room temperature until the formation of a clear solution and then 1,3-dicyclohexylcarbodiimide (16 ml, 1.0 N in dichloromethane, 16.0 mmole) was added. The mixture was stirred at room temperature overnight. The white solid was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform (100 ml), and the solution was washed by saturated NaHCO3 (100 ml) and H2O (100 ml). The organic solvent was evaporated to dryness to give a yellow glass. This yellow glass was passed through a silica column with MeOH/EtOAc (5/95) to give a yellow glass as product 8 (5.5 g, 70% yield). The compound was characterized as NMR and MS as follows: 1) C-NMR (CDCl3): 11.983, 12.861, 13.729, 20.117, 23.550, 30.055, 35.951, 41.494, 45.291, 52.196, 52.087, 57.051, 73.411, 75.309, 99.049, 116.801, 122.420, 123.437, 125.719, 127.671, 128.283, 134.187, 146.465, 147.220, 162.451, 163.470 ppm; 2) H-NMR (CDCl3): 1.244 (s, 3H), 1.790 (m, 4H), 2.052 (s, 3H), 2.119 (s, 3H), 2.157 (s, 3H), 2.9-2.6 (m, 8H), 3.586 (s, 3H), 3.62 (b, 2H), 3.72 (b, 2H), 4.813 (s, 2H), 4.825 (s, 2H), 7.726 (m, 2H), 7.803 (m, 2H) ppm; and 3) MS (ESI): 566.4 [M+H]+, 588.4 [M+Na]+.

1. stirringThe mixture was stirred at room temperature overnight
2. customThe white solid was removed by filtration
3. customthe solvent was evaporated under reduced pressure
4. dissolutionThe residue was dissolved in chloroform (100 ml)
5. washthe solution was washed by saturated NaHCO3 (100 ml) and H2O (100 ml)
6. customThe organic solvent was evaporated to dryness
7. customto give a yellow glass

ORD record

ord-59efdace374e48a88e62694aa2841c54

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384558B2