Trifluoromethanesulfonic anhydride → HCID 18797032, compound

HRID 1003708Notes

Reaction equation

HRID 1003708 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].[C:16]([C:18]1[CH:19]=[C:20]([C:24]2[CH:47]=[CH:46][C:27]([C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:44][CH2:43][C:42]4[C:37](=[CH:38][C:39](O)=[CH:40][CH:41]=4)[CH2:36]3)=[O:29])=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1)#[N:17]>N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[C:16]([C:18]1[CH:19]=[C:20]([C:24]2[CH:47]=[CH:46][C:27]([C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:44][CH2:43][C:42]4[C:37](=[CH:38][C:39]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:40][CH:41]=4)[CH2:36]3)=[O:29])=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1)#[N:17]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 18797012HCID 18797012, compound

Product 1

HCID 18797032HCID 18797032, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.21 ml, 1.25 mmol) was added dropwise with stirring to an ice cooled solution of 2-(4-(4-(3-cyanophenyl)benzoylamino)butyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (0.41 g, 0.96 mmol) in anhydrous pyridine (5 ml). After stirring at room temperature for 18 h. the mixture was poured into 10% aqueous copper (II) sulphate (100 ml). The mixture was extracted with ethyl acetate (2×50 ml) and the combined extracts 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 gel using 10-100% ethyl acetate-hexane gradient elution to afford the title compound (0.263 g, 49%).

Workup

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

Sources & evidence

ORD record
ord-c5147f969b30476dabf129823cabc083
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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