Trifluoromethanesulfonic anhydride → HCID 17866228, compound

HRID 1856794Notes

Reaction equation

HRID 1856794 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])/[CH:33]=[CH:34]/[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:24]2)=[CH:19][CH:18]=1>N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[C:35]1(/[CH:34]=[CH:33]/[C:32]([NH:31][CH2:30][CH2:29][CH2:28][CH2:27][N:23]2[CH2:22][CH2:21][C:20]3[C:25](=[CH:26][C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:18][CH:19]=3)[CH2:24]2)=[O:41])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 17866244HCID 17866244, compound

Product 1

HCID 17866228HCID 17866228, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.26 ml, 1.52 mmol) was added dropwise with stirring to an ice cooled solution of (E)-7-hydroxy-2-(4-(3-phenylpropenoyl)aminobutyl)-1,2,3,4-tetrahydroisoquinoline (0.41 g, 1.17 mmol) in anhydrous pyridine (5 ml). After stirring at room temperature for 18 h the reaction mixture was poured into 10% aqueous copper (II) sulfate (100 ml). The mixture was extracted with ethyl acetate (2×75 ml). Combined extracts were washed with 10% aqueous copper (II) sulfate (2×50 ml), water (50 ml), dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica using 10-100% ethyl acetate-hexane gradient elution to afford the title compound (0.205 g, 43%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×75 ml)
  2. washCombined extracts were washed with 10% aqueous copper (II) sulfate (2×50 ml), water (50 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica using 10-100% ethyl acetate-hexane gradient elution

Sources & evidence

ORD record
ord-7db12dd3d0d742ae925fd4611e906fd8
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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