Sodium Azide → Benzyl tert-butyl (3-azidopropane-1,2-diyl)biscarbamate

HRID 1504845Notes

Reaction equation

CS(O[CH2:6][CH:7]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8][NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:6][CH:7]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:8][NH:9][C:10](=[O:11])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+:29]=[N-:30]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate (20.0 g, 49.7 mmol) in DMF (400 mL) was added sodium azide (8.0 g, 120 mmol). The reaction mixture was heated to 50° C. After 24 hours, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The organic layers were concentrated under reduced pressure to afford benzyl tert-butyl (3-azidopropane-1,2-diyl)biscarbamate. The material was used without purification. MS ESI calc'd. for C16H24N5O4 [M+H]+ 350. found 350.

Workup

temperaturethe reaction mixture was cooled to ambient temperature
extractionextracted with ethyl acetate
concentrationThe organic layers were concentrated under reduced pressure

Sources & evidence

ORD record: ord-b96afe76cf4248db8cdcc58aec1b9ea0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

Loading…