Triethylamine → 2-(N-tert-butyloxycarbonyl-2-aminoethylamino)ethyl methyl sulfone

HRID 2425597Notes

Reaction equation

HRID 2425597 reaction equation
[CH:1]([S:3]([CH3:6])(=[O:5])=[O:4])=[CH2:2].Cl.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH2:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>CO>[CH3:6][S:3]([CH2:1][CH2:2][N:15]([CH2:16][CH2:17][NH2:18])[C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19354Methyl vinyl sulfoneHCID 187200tert-Butyl N-(2-aminoethyl)carbamate hydrochloride

Product 1

HCID 866023162-(N-tert-butyloxycarbonyl-2-aminoethylamino)ethyl methyl sulfoneYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl vinyl sulfone (0.42 mL, 4.8 mmol) was added dropwise to a cooled solution of N-tert-butyloxycarbonyl-1,2-ethylenediamine hydrochloride (1.00 g, 5.1 mmol) and triethylamine (1.4 mL, 10.7 mmol) in methanol (20 mL). The reaction was stirred at room temperature for 18 h and concentrated. Purification of the crude residue by chromatography over silica gel using 0-5% methanol in methylene chloride gave 2-(N-tert-butyloxycarbonyl-2-aminoethylamino)ethyl methyl sulfone (1.05 g, 77%).

Workup

  1. concentrationconcentrated
  2. customPurification of the crude residue by chromatography over silica gel using 0-5% methanol in methylene chloride

Sources & evidence

ORD record
ord-164d6cbacb4d4826b11ccfe5251b0774
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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