Triethylamine → HCID 22346254, compound

HRID 626930Notes

Reaction equation

HRID 626930 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.Cl[CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH:21]([S:22]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])(=[O:24])=[O:23])=[CH2:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 187201N-BOC-ethylenediamine

Product 1

HCID 22346254HCID 22346254, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-(2-aminoethyl)carbamate (5.00 g, 31.2 mmol) was dissolved in dry dichloromethane (50 mL). Triethylamine (7.02 g, 68.7 mmol) was added and the mixture was cooled in an ice bath, with stirring. 2-Chloroethanesulfonyl chloride (5.09 g, 31.2 mmol) was added dropwise, and the ice bath was removed. The mixture was stirred and allowed to warm to room temperature, stirring overnight. The mixture was partitioned between dichloromethane (150 mL) and 1.5M aqueous sodium carbonate solution (75 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to give the title compound (7.81 g, quantitative, contains 0.4 equivalents of triethylamine) as a colourless oil. δH (d6-DMSO) 6.53 (dd, 1H, J 16.6, 9.9 Hz), 6.24 (d, 1H, J 16.6 Hz), 5.95 (d, 1H, J 9.9 Hz), 5.06 (br s, 2H), 3.31-3.27 (m, 2H), 3.16-3.12 (m, 2H), 1.45 (s, 9H). LCMS (ES+) 251 (M+H)+.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customthe ice bath was removed
  3. stirringThe mixture was stirred
  4. stirringstirring overnight
  5. customThe mixture was partitioned between dichloromethane (150 mL) and 1.5M aqueous sodium carbonate solution (75 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8bbd2a103f64594bc4be5552952b69d
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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