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

HRID 8530Notes

Reaction equation

HRID 8530 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-3c0fb83b039044d3acf999e92efa2059
Source dataset
uspto-grants-2006_08
Patent number
US07087759B2

Reaction notes

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