Sodium Azide → HCID 118453386, compound

HRID 1056927Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[C:16](=[O:22])[N:15]([CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:14]1[C:32]3[CH:33]=[C:34]4[O:42][CH2:41][O:40][C:35]4=[CH:36][C:37]=3[C:38](=[O:39])[C:13]2=1>CS(C)=O.C(Cl)(Cl)Cl>[N:1]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[C:16](=[O:22])[N:15]([CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:14]1[C:32]3[CH:33]=[C:34]4[O:42][CH2:41][O:40][C:35]4=[CH:36][C:37]=3[C:38](=[O:39])[C:13]2=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium azide (0.021 g, 0.22 mmol) and compound 19 (0.128 g, 0.22 mmol) were diluted with DMSO (4 mL), and the mixture was heated at 100° C. for 2 h. The mixture was diluted to a volume of 200 mL with CHCl3, washed with H2O (2×60 mL) and saturated aq NaCl (50 mL), dried over anhydrous sodium sulfate, and concentrated. The resulting residue was purified by flash column chromatography (SiO2, ˜40 g), eluting with a gradient of 0.5% MeOH in CHCl2, to yield the product 21 as a solid (0.036 g, 60%). The solid was used for next step without further purification. ESIMS m/z 548 (MH+); HRESIMS m/z 548.2141 (MH+), calcd for C28H30N5O7 548.2145.

Workup

washwashed with H2O (2×60 mL) and saturated aq NaCl (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe resulting residue was purified by flash column chromatography (SiO2, ˜40 g)
washeluting with a gradient of 0.5% MeOH in CHCl2

Sources & evidence

ORD record: ord-5c9b3a97950d4484ad4a64a226719723
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399660B2

Reaction notes

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