Trifluoroacetic acid → HCID 9862380, compound

HRID 1392138Notes

Reaction equation

HRID 1392138 reaction equation
COC1C=C(OC)C=CC=1C[O:6][N:7](CC1C(OC)=CC(OC)=CC=1OC)[C:8](=[O:27])[CH2:9][CH2:10][S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])=[O:12].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[OH:6][NH:7][C:8](=[O:27])[CH2:9][CH2:10][S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22719709HCID 22719709, compound

Product 1

HCID 9862380HCID 9862380, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,4-dimethoxybenzyloxy)-N-(2,4,6-trimethoxybenzyl)-3-[4-(4-fluorophenyl)piperazine-1-sulfonyl]propionamide (125 mg, 0.19 mmol) in dichloromethane (2 ml) was added triethylsilane (66 μl, 0.42 mmol) and trifluoroacetic acid (150 μl). The mixture was stirred at room temperature for 4 hours. The solvents were evaporated in vacuo. The residue was purified by chromatography on silica (eluant:dichloromethane, then ethyl acetate then dichloromethane −10% MeOH) to give 35 mg of the title compound.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customThe residue was purified by chromatography on silica (eluant

Sources & evidence

ORD record
ord-df11eeb1f4a843918a3f128c975d11da
Source dataset
uspto-grants-2008_03
Patent number
US07342020B2

Reaction notes

Loading…