1,2-Dichloroethane → HCID 57446126, compound

HRID 1170788Notes

Reaction equation

HRID 1170788 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[N:23]([CH2:26][C:27](O)=[O:28])=[N+:24]=[N-:25].C([O-])(O)=O.[Na+].C(Cl)CCl>CN(C=O)C>[N:23]([CH2:26][C:27](=[O:28])[NH:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[N+:24]=[N-:25]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 155605Azidoacetic acidHCID 516892Sodium BicarbonateHCID 11989604Boc-TOTA

Product 1

HCID 57446126HCID 57446126, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing tert-butyl 3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propylcarbamate (amine, 160 mg, 0.5 mmol), 2-azidoacetic acid (56 mg, 0.55 mmol, in 50% DCM solution), NaHCO3 (168 mg, 2 mmol), and 1 mL DMF was added EDC (115 mg, 0.6 mmol). The mixture was stirred at rt for 3 h and concentrated in vacuo. The crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane) to afford compound 141 as a clear oil (130 mg, 65%). MS (ESI) m/z 426 (M+Na+).

Workup

  1. customTo a 25 mL round bottomed flask equipped with a magnetic stir bar
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane)

Sources & evidence

ORD record
ord-145679f0c34542619a42b2e27039dba5
Source dataset
uspto-grants-2010_11
Patent number
US07829063B2

Reaction notes

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