Reaction #8626

ord-3c0fb83b039044d3acf999e92efa2059

Reaction equation

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

Reactants

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

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated in vacuo
  2. 2
    workup.DISSOLUTIONThe crude product is dissolved in dichloromethane
  3. 3
    Washthe organic layer washed with saturated sodium bicarbonate
  4. 4
    Otherdried
  5. 5
    Concentrationconcentrated in vacuo

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087759B2uspto-grants-2006_08