Dimethylformamide → HCID 22907807, compound

Temperature

60 °C

7-azidoheptanoic acid (64) was synthesized from 7-bromoheptanoic acid 63 as shown above. To 914 mg of 7-bromoheptanoic acid (63) (commercially available from Matrix Scientific, Columbia, S.C.) (4.4 mmol) was added 15 mL anhydrous DMF. To the stirring solution was added 914 mg NaN3 (14 mmol, 3.2 eq) at room temperature. The clear solution was warmed to 60° C. for a period of 6 h. The solution was then cooled to room temperature and diluted with 50 mL CH2Cl2. The organic layer was washed with cold 1N HCl (7×50 mL) and brine (2×50 mL), then dried over anhydrous Na2SO4. Filtration and removal of solvent afforded 709 mg crude 7-azidoheptanoic acid 64 in 94% yield which was of suitable purity for continued progression enroute to materials 65 and 66. An NMR analysis was performed where: 1H NMR (400 MHz, CDCl3) δ 11.55 (bs, 1H), 3.14 (t, J=6.8 Hz, 2H), 2.22 (t, J=7.2 Hz, 2H), 1.56-1.45 (m, 4H), 1.30-1.24 (m, 4H); 13C NMR (400 MHz, CDCl3) δ 178.3, 51.1, 33.7, 28.5, 28.4, 26.2, 24.4. HRMS (ESI) calculated. for C7H13N3O2 (M−H): 170.0930, measured: 170.0930.

1. temperatureThe solution was then cooled to room temperature
2. washThe organic layer was washed with cold 1N HCl (7×50 mL) and brine (2×50 mL)
3. dry with materialdried over anhydrous Na2SO4
4. filtrationFiltration and removal of solvent

ORD record

ord-3d0c99df58cc4d2fa2384dea23c750cc

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465544B2