(Boc)2NN(Boc)CH2CONHCH2CH2N3 → H2Nnhch2conhch2CH2N3

HRID 884349Notes

Reaction equation

HRID 884349 reaction equation
[N:1]([N:16]([CH2:24][C:25]([NH:27][CH2:28][CH2:29][N:30]=[N+:31]=[N-:32])=[O:26])C(OC(C)(C)C)=O)(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>Cl.O1CCOCC1>[NH2:1][NH:16][CH2:24][C:25]([NH:27][CH2:28][CH2:29][N:30]=[N+:31]=[N-:32])=[O:26]

Participants

4

Reactant 1

HCID 131729880(Boc)2NN(Boc)CH2CONHCH2CH2N3

Product 1

HCID 90814832H2Nnhch2conhch2CH2N3Yield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Azide 5 (4.66 g, 10.17 mmol) was dissolved in 4 N HCl in dioxane (200 mL), and the solution was stirred at room temperature for 5 h. Solvent was removed under reduced pressure, and the residue was dissolved in water (15 mL) and purified by cation-exchange chromatography (Dowex 50WX8-200 ion-exchange resin, 1 M NH4OH) to give H2NNHCH2CONHCH2CH2N3 as a yellow oil (1.52 g, 95%). HRMS (ESI) [M+Na]+ calcd for C4H10N6ONa, 181.0814; found, 181.0805; 1H NMR (300 MHz, d6-DMSO) δ 8.03 (app bs, 1H), 3.80-3.40 (bs, 3H), 3.40-3.34 (m, 2H), 3.32-3.24 (m, 2H), 3.16 (s, 2H); 13C NMR (75 MHz, d6-DMSO) δ 171.2, 57.1, 50.0, 37.8.

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in water (15 mL)
  3. custompurified by cation-exchange chromatography (Dowex 50WX8-200 ion-exchange resin, 1 M NH4OH)

Sources & evidence

ORD record
ord-eb5785b1e00f4091a3daccb85f266f38
Source dataset
uspto-grants-2012_08
Patent number
US08242058B2

Reaction notes

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