Reacción #3237

ord-0a45a609ac2e45e08721ea94db9274b3

Ecuación de reacción

CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=O
Boc-valineamide
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent
CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=S
title compound
Rendimiento 70.0%
CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=S
Boc-valinethioamide
Rendimiento 70.0%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was evaporated
  2. 2
    Otrothe residue chromatographed (silica, 2.5% methanol/dichloromethane)

Procedimiento

Boc-valineamide (0.5 g) was stirred in dry THF at room temperature under argon. Lawesson's reagent (1.56 g, 0.6 eq) was added and the mixture was stirred overnight. The solvent was evaporated and the residue chromatographed (silica, 2.5% methanol/dichloromethane) to give the title compound as a white solid (0.373 g, 70%). NMR(CDCl3) δ 8.59 (1H, br s), 8.09 (1H, br s), 5.41 (1H, d (br)), 4.20 (1H, dd), 1.99 (1H, m), 1.39 (9H, s), 0.90 (6H, m).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05733882uspto-grants-1998_03