Reacción #710533

ord-9f37ed79177d468bb1f871f948e20772

Ecuación de reacción

CS(=O)(=O)O
Methanesulfonic acid
C=C[C@@H]1C[C@]1(NC(=O)OC(C)(C)C)C(=O)O
(1R,2S)-1-(tert-butoxycarbonylamino)-2-vinyl-cyclopropanecarboxylic acid
CCN(CC)CC
triethylamine
C=C[C@@H]1C[C@]1(N)C(=O)O
titled compound
C=C[C@@H]1C[C@]1(N)C(=O)O
(1R,2S)-1-amino-2-vinyl-cyclopropanecarboxylic acid

Condiciones de reacción

Temperatura
25°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroa solid was precipitated
  2. 2
    OtroThe solid was sufficiently precipitated
  3. 3
    workup.STIRRINGthe solution was stirred at 25° C. for 30 minutes
  4. 4
    OtroThereafter, the solid was separated by filtration under reduced pressure
  5. 5
    LavadoThe solid was washed with methylene chloride (5 mL)
  6. 6
    Otrodrying

Procedimiento

Methanesulfonic acid (576 mg, 6 mmol) was added to a solution of (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinyl-cyclopropanecarboxylic acid (1135 mg, 5 mmol) and methylene chloride (5 mL), and the mixture was stirred at 25° C. for 3 hours. When triethylamine (708 mg, 7 mmol) was added thereto, a solid was precipitated. The solid was sufficiently precipitated, and then the solution was stirred at 25° C. for 30 minutes. Thereafter, the solid was separated by filtration under reduced pressure. The solid was washed with methylene chloride (5 mL), and then was subjected to vacuum drying. Thereby, the titled compound was produced as a white solid (665 mg, yield of 100%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09302980B2uspto-grants-2016_04