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

HRID 269613Notes

Reaction equation

CS(O[CH2:6][C@@H:7]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O>[C:15]([O:14][C:12](=[O:13])[NH:11][CH2:10][CH2:9][CH2:8][C@H:7]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][N:27]=[N+:28]=[N-:29])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 218 mg (0.55 mmol) of (2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl methanesulfonate (Example 84A) in 15 ml of dimethylformamide is mixed with 36 mg (0.55 mmol) of sodium azide and stirred at 70° C. for 12 h. Most of the solvent is removed by distillation in vacuo, and the residue is diluted with ethyl acetate. The mixture 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

customMost of the solvent is removed by distillation in vacuo
additionthe residue is diluted with ethyl acetate
washThe mixture 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-6e863506ecdb4d449332d90aef9ffac8
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446102B2

Reaction notes

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