2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 18765910, compound

HRID 481011Notes

Reaction equation

HRID 481011 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-])=O)[NH:12][C:11]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:10]1[C:35]([O:37][CH3:38])=[O:36].C(N(CC)C(C)C)(C)C.[F:48][C:49]([F:60])([F:59])[CH2:50]OS(C(F)(F)F)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][CH2:50][C:49]([F:60])([F:59])[F:48])[NH:12][C:11]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:10]1[C:35]([O:37][CH3:38])=[O:36]

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 18765904HCID 18765904, compound

Product 1

HCID 18765910HCID 18765910, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of dimethyl 4-(2,6-dichlorophenyl)-2-(2-methoxy-2-oxoethyl)-6-[2-(2-nitrophenyl)ethyl]-1,4-dihydro-3,5-pyridinedicarboxylate (example 10, 1.56 g/2.92 mmol) and N,N-diisopropylethylamine (3.78 g/29.2 mmol) in toluene (50 ml) was added trifluoromethanesulfonic acid 2,2,2-trifluoroethyl ester (6.78 g/29.2 mmol) at room temperature. The reaction mixture was refluxed at 130° C. for 1 day. The reaction was quenched with water and the separated organic layer was washed with sat.NaHCO3 and brine, dried over MgSO4, filtered and concentrated to afford a crude mixture. This crude was purified by column chromatography on silica gel (Hexane:EtC,Ac=2:1) to afford a pale yellow oil (1.34 g/75%).

Workup

  1. customThe reaction was quenched with water
  2. washthe separated organic layer was washed
  3. dry with materialNaHCO3 and brine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34f47479c6224de7a2f4588a5821e260
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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