Reacción #8626

ord-3c0fb83b039044d3acf999e92efa2059

Ecuación de reacción

CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCO[Si](C)(C)C(C)(C)C)C1=O
2-[3-[2-(tert-butyldimethylsilanyloxy)ethyl]-4-(2-nitrobenzene-sulfonyl)-2-oxo-piperazin-1-yl]-N-methyl-3-naphthalen-2-yl propionamide
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CNC(=O)C(Cc1ccc2ccccc2c1)N1CCNC(CCO[Si](C)(C)C(C)(C)C)C1=O
desired product
CNC(=O)C(Cc1ccc2ccccc2c1)N1CCNC(CCO[Si](C)(C)C(C)(C)C)C1=O
2-{3-[2-(tert-Butyldimethylsilanyloxy)ethyl]-2-oxo-piperizin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide

Reactantes

CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCO[Si](C)(C)C(C)(C)C)C1=O
2-[3-[2-(tert-butyldimethylsilanyloxy)ethyl]-4-(2-nitrobenzene-sulfonyl)-2-oxo-piperazin-1-yl]-N-methyl-3-naphthalen-2-yl propionamide
O=C(O)C(F)(F)F
trifluoroacetic acid

Reactivos

Ninguno

Disolventes

ClCCl
dichloromethane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated in vacuo
  2. 2
    workup.DISSOLUTIONThe crude product is dissolved in dichloromethane
  3. 3
    Lavadothe organic layer washed with saturated sodium bicarbonate
  4. 4
    Otrodried
  5. 5
    Concentraciónconcentrated in vacuo

Procedimiento

2-[3-[2-(tert-butyldimethylsilanyloxy)ethyl]-4-(2-nitrobenzene-sulfonyl)-2-oxo-piperazin-1-yl]-N-methyl-3-naphthalen-2-yl propionamide, 57, (6.5 g, 10 mmol), trifluoroacetic acid (5 mL), and dichloromethane (50 mL) is stirred at room temperature for 2 hours and then concentrated in vacuo. The crude product is dissolved in dichloromethane and the organic layer washed with saturated sodium bicarbonate, dried, and concentrated in vacuo to afford the desired product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07087759B2uspto-grants-2006_08