Sodium Azide → tert-butyl-{(4S)-5-azido-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

HRID 1441986Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][C@@H:11]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=O)=O>CN(C)C=O>[N:1]([CH2:10][C@@H:11]([NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 70 °C

Procedure

36 mg (0.55 mmol) of sodium azide are added to a solution of 218 mg (0.55 mmol) of (2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl methanesulfonate (Example Z7) in 15 ml of dimethylformamide and the mixture is stirred at 70° C. for 12 h. Most of the solvent is distilled off in vacuo, and the residue is diluted with ethyl acetate. The solution is washed several times with a saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness in vacuo. The product is reacted without further purification.

Workup

distillationMost of the solvent is distilled off in vacuo
additionthe residue is diluted with ethyl acetate
washThe solution is washed several times with a saturated sodium bicarbonate solution
dry with materialdried over magnesium sulfate
customevaporated to dryness in vacuo
customThe product is reacted without further purification

Sources & evidence

ORD record: ord-02383e178af146cbb96c3de92084cb35
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655643B2

Reaction notes

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