Sodium Azide → Tert-butyl n-(2-azido-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamate

HRID 1923979Notes

Reaction equation

HRID 1923979 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10](OS(C)(=O)=O)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C.C(Cl)Cl>[N:25]([CH:10]([CH2:11][NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14839452N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane

Product 1

HCID 15186001Tert-butyl n-(2-azido-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl N-(3-{[(tert-butoxy)carbonyl]amino}-2-(methanesulfonyloxy)propyl)carbamate XL (2.31 g, 6.6 mmol) in DMF was added NaN3. The mixture was heated overnight at 60° C., diluted with DCM and washed with 10% Na2S2O3 (5×), 5% NaHCO3, brine and dried over MgSO4. The solvent was evaporated under vacuum to give crude product (1.75 g). The product was purified on a silica gel column (1:10 EtOAc:hexane) to give the pure tert-butyl N-(2-azido-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamate XLI as white crystals (1.33 g, 4.2 mmol, 67% yield). 1H NMR (CDCl3) 1.47 (s, 18H), 3.07-3.26 (m, 2H), 3.27-3.53 (m, 2H), 3.59-3.75 (m, 1H), 5.06 (brs, 2H); ESIMS found for C13H25N5O4 m/z 316 (M+H).

Workup

  1. washwashed with 10% Na2S2O3 (5×), 5% NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated under vacuum
  4. customto give crude product (1.75 g)
  5. customThe product was purified on a silica gel column (1:10 EtOAc:hexane)

Sources & evidence

ORD record
ord-3b40ae41820e47ab89ae731648a68df0
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

Loading…