Diethyl [(3-azidopropane-1-sulfonyl)amino]propanedioate → Diethyl [(3-aminopropane-1-sulfonyl)amino]propanedioate

HRID 1375206Notes

Reaction equation

HRID 1375206 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([NH:11][S:12]([CH2:15][CH2:16][CH2:17][N:18]=[N+]=[N-])(=[O:14])=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([NH:11][S:12]([CH2:15][CH2:16][CH2:17][NH2:18])(=[O:13])=[O:14])[C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH3:10]

Participants

5

Reactant 2

HCID 21079549Diethyl [(3-azidopropane-1-sulfonyl)amino]propanedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 21079546Diethyl [(3-aminopropane-1-sulfonyl)amino]propanedioateYield 105.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-azidopropanesulfonamidomalonate diethyl ester (27.60 g, 0.086 mol,) in ethanol (70 mL) and 1 g of Pd/C (10%) were placed in a Parr hydrogenation apparatus under 60 psi H2 for 8 hours. The hydrogen was replenished every 2 hours. The mixture was filtered through a pad of Celite and a solution of 1 N HCl in ethanol (10 mL) was added to the filtrate. The solvent was removed in vacuo and the residue was purified by column chromatography on Al2O3 using CH2Cl2/MeOH (4/1, v/v) to give 26.84 g of the title compound as the hydrochloride salt: 1H NMR (CDCl3) δ 1.30 (t, 6, CH3), 2.12 (m, 2, OCH2CH3), 3.21 (t, 2, CH2), 3.50 (t, 2, CH2), 4.26 (m, 4, OCH2CH3), 4.84 (d,1, CH), 6.09 (d, 1, NH), 8.29 (br.s, 2, NH3). 13C NMR (CDCl3) 613.6, 26.3, 42.5, 51.2, 58.5, 62.7, 165.9.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. additiona solution of 1 N HCl in ethanol (10 mL) was added to the filtrate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography on Al2O3

Sources & evidence

ORD record
ord-2234edaa3e2d4f6daf76f0a5d1dc6719
Source dataset
uspto-grants-2007_01
Patent number
US07166733B2

Reaction notes

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