Potassium Carbonate → HCID 86611783, compound

HRID 505006Notes

Reaction equation

HRID 505006 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O[CH2:22][CH2:23][N:24]=[N+:25]=[N-:26])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[N+](C)([O-])=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:22][CH2:23][N:24]=[N+:25]=[N-:26])[CH2:22][CH2:23][N:24]=[N+:25]=[N-:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 187201N-BOC-ethylenediamineHCID 11379486HCID 11379486, compound

Product 1

HCID 86611783HCID 86611783, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino)ethylamine (10 mg; 0.6 mmol), 2-azidoethyl p-toluenesulphonate (370 mg; 1.5 mmol; 1.25 equiv) and potassium carbonate (2.4 mmol, 2 equiv) is taken to reflux in nitromethane for 16 hours. The solution is then concentrated and the residual product dissolved in dichloromethane (10 ml), washed with water (5 ml) and purified by column chromatography (EtOAc-hexane 1:3) leading to the title product (130 mg, 70%).

Workup

  1. concentrationThe solution is then concentrated
  2. dissolutionthe residual product dissolved in dichloromethane (10 ml)
  3. washwashed with water (5 ml)
  4. custompurified by column chromatography (EtOAc-hexane 1:3)

Sources & evidence

ORD record
ord-3d73d60a25bf4cc3ad6bd8f6f1abff8b
Source dataset
uspto-grants-2010_08
Patent number
US07781417B2

Reaction notes

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