Trifluoroacetic acid → 2-{3-[2-(tert-Butyldimethylsilanyloxy)ethyl]-2-oxo-piperizin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide

HRID 1072630Notes

Reaction equation

HRID 1072630 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH:11]1[N:16](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:15][CH2:14][N:13]([CH:29]([CH2:34][C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=2)[C:30]([NH:32][CH3:33])=[O:31])[C:12]1=[O:45])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[Si:1]([O:8][CH2:9][CH2:10][CH:11]1[NH:16][CH2:15][CH2:14][N:13]([CH:29]([CH2:34][C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=2)[C:30]([NH:32][CH3:33])=[O:31])[C:12]1=[O:45])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 220156972-[3-[2-(Tert-butyldimethylsilanyloxy)ethyl]-4-(2-nitrobenzene-sulfonyl)-2-oxo-piperazin-1-yl]-n-methyl-3-naphthalen-2-yl propionamide

Product 1

HCID 208063272-{3-[2-(tert-Butyldimethylsilanyloxy)ethyl]-2-oxo-piperizin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude product is dissolved in dichloromethane
  3. washthe organic layer washed with saturated sodium bicarbonate
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-683232e293804164993665520b1ae068
Source dataset
uspto-grants-2005_06
Patent number
US06911447B2

Reaction notes

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