Reacción #1884974

ord-4a965e8fa45c4fbeb1dc82ffd40d8848

Ecuación de reacción

C=C[C@@H]1C[C@]1(NC(=O)OC(C)(C)C)C(=O)NS(=O)(=O)C1CC1
product
C=C[C@@H]1C[C@]1(NC(=O)OC(C)(C)C)C(=O)NS(=O)(=O)C1CC1
cyclopropanesulfonic acid (1-(R)-tert-butoxycarbonylamino-2-(S)-vinylcyclopropanecarbonyl)-amide
ClCCl
dichloromethane
C=C[C@@H]1C[C@]1(N)C(=O)NS(=O)(=O)C1CC1.Cl
title compound
C=C[C@@H]1C[C@]1(N)C(=O)NS(=O)(=O)C1CC1.Cl
cyclopropanesulfonic acid (1-(R)-amino-2-(S)-vinyl-cyclopropanecarbonyl)amide HCl salt

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe volatiles were removed in vacuo
  2. 2
    Concentraciónconcentrated in vacuo
  3. 3
    OtroThe resulting mixture was triturated from pentane
  4. 4
    Filtraciónfiltered

Procedimiento

A solution of the product of Step 2 (3.5 g, 10.6 mmol) in dichloromethane (35 mL) and TFA (32 mL) was stirred at room temperature for 1.5 hours. The volatiles were removed in vacuo and the residue suspended in 1N HCl in diethyl ether (20 mL) and concentrated in vacuo. This procedure was repeated once. The resulting mixture was triturated from pentane and filtered to give the title compound as a hygroscopic, off-white solid (2.60 g, 92%). 1H NMR: (DMSO-d6) 1.01-1.15 (m, 4H), 1.69-1.73 (m, 1H), 1.99-2.02 (m, 1H), 2.38 (q, J=9 Hz, 1H), 2.92-2.97 (m, 1H), 5.20 (d, J=11 Hz, 1H), 5.33 (d, J=17 Hz, 1H), 5.52-5.59 (m, 1H), 9.17 (br s, 3H); MS m/z 231 (M++H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08343477B2uspto-grants-2013_01