Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Magnesium monoxide | HCID 6850729 | — |
| Reactant | Iodo benzene diacetate | HCID 12217721 | — |
| Reactant | HCID 67408933 | HCID 67408933 | — |
| Catalyst | 2,2'-[1,3-Phenylenebis(methylene)]bis(2-methylpropanoic acid)--rhodium (1/1) | HCID 72750008 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67408611 | HCID 67408611 | 15% |
| Product | HCID 67408933 | HCID 67408933 | — |
Reaction Steps
(S)-2-(6-Heptyloxyquinazolin-2-yl)propyl carbamate (14, 350 mg, 0.0010 mol) was dissolved in toluene (20 mL, 0.2 mol), followed by magnesium monoxide (93.9 mg, 0.00233 mol), iodobenzene diacetate (359 mg, 0.00111 mol) and finally Rh2(esp)2 (35 mg, 0.000046 mol). The reaction mixture was then heated at 40° C. for 3 days. DCM was added to the reaction mixture, and the reaction mixture was filtered. The crude mixture was then purified via chromatography (SiO2, 12 g, 0-80% ethyl acetate/hexanes) to give 53 mg of the desired product (15%) and 215.0 mg of 14. 1H NMR (CHLOROFORM-d) δ: 9.27 (s, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.58 (dd, J=9.2, 2.6 Hz, 1H), 7.15 (d, J=2.5 Hz, 1H), 6.19 (br. s., 1H), 5.18 (d, J=8.5 Hz, 1H), 4.49 (d, J=8.8 Hz, 1H), 4.11 (t, J=6.5 Hz, 2H), 1.80-1.97 (m, 2H), 1.76 (s, 3H), 1.21-1.60 (m, 8H), 0.91 (t, J=6.7 Hz, 3H). MS (M+1): 344.30.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08349849B2 |
|---|
| Source dataset | uspto-grants-2013_01 |
|---|
| ORD ID | ord-2c0404732a3943ee9b21965ffc795692 |
|---|
| Source note | uspto-grants-2013_01 |
|---|
