Реакция #40285

ord-81c8b3c0439348328e900f92313d677b

Уравнение реакции

O
Water
CC(C)(C)OC(=O)NCCC(=O)O
N-Boc-β-alanine
CC(C)(C)OC(=O)NCCC(=O)O
3-tert-Butoxycarbonylamino-propionic Acid
C#CCN
propargyl amine
CC(C)N=C=NC(C)C
Diisopropyl-carbodiimide
C#CC(N)=O.CC(C)(C)OC(=O)NCCC(=O)O
N-Boc-β-alanine Propargyl Amide

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Экстракцияthe product was extracted into EtOAc (3×30 mL)
  2. 2
    СушкаThe combined EtOAc was dried (Na2SO4)
  3. 3
    Другоеevaporated
  4. 4
    ДругоеThe crude product was purified by silica column chromatography
  5. 5
    Промывкаeluting with EtOAc

Методика

N-Boc-β-alanine (1a) (1.05 g, 5.5 mmol) and propargyl amine (0.90 g, 16.5 mmol) were dissolved in THF (10 mL). Diisopropyl-carbodiimide (DIC, 695 g, 5.5 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. Water was added (20 mL) and the product was extracted into EtOAc (3×30 mL). The combined EtOAc was dried (Na2SO4) and evaporated. The crude product was purified by silica column chromatography eluting with EtOAc:Heptane gradient (2:3)-(3:2.5) (v/v). Product yield 0.925 g, 74%.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07727713B2uspto-grants-2010_06