Sodium Azide → HCID 86699888, compound

HRID 1502223Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][N:9]1[C:15](=[O:16])[CH2:14][CH:13]2[C:17](=[O:18])[CH:10]1[CH:11]=[CH:12]2.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][N:9]1[C:15](=[O:16])[CH2:14][CH:13]2[C:17](=[O:18])[CH:10]1[CH:11]=[CH:12]2)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirring solution of 3b (100 mg, 0.302 mmol) in DMF (10 mL) was added sodium azide (98 mg, 1.51 mmol). The solution was allowed to stir at 65° C. overnight. After cooling to room temperature, the solution was diluted with water (10 mL) and extracted with EtOAc (3×15 mL). The combined organic phase was dried over Na2SO4. The drying agent was removed by filtration and the solvent was removed under reduced pressure to afford 3c as a clear oil (73 mg, 83%). The oil was taken on without further purification immediately, as 3c was found to be unstable. 1H-NMR (CDCl3, 300 MHz): δ 6.70 (dd, J=5.8, 1.0 Hz, 1H), 6.49 (dd, J=6.0, 1.7 Hz, 1H), 5.47 (d, J=1.1 Hz, 1H), 4.50 (d, J=1.6 Hz, 1H), 3.92 (ABX2, JAX=JBX=6.7 Hz, JAB=9.2 Hz, 2H), 3.27 (t, J=7.0 Hz, 2H), 1.71-1.56 (m, 4H), 1.48 (s, 3H), 1.48-1.39 (m, 4H), 1.04 (s, 3H). 13C-NMR (CDCl3, 75 MHz): δ 175.4, 135.3, 134.6, 90.6, 87.1, 75.3, 51.2, 48.8, 28.5, 27.9, 26.7, 26.3, 25.3, 19.6. HRESI-MS calcd for C14H22N4O3 [M+H]+ 295.1765. found 295.1758.

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (3×15 mL)
dry with materialThe combined organic phase was dried over Na2SO4
customThe drying agent was removed by filtration
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-0ef54ef8eab947ecb7b63a0431551e5e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206271B2

Reaction notes

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