Triethylamine → HCID 60155357, compound

HRID 1506868Notes

Reaction equation

HRID 1506868 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11].C(N(CC)CC)C.[O:22](S(C(F)(F)F)(=O)=O)[S:23]([C:26]([F:29])([F:28])[F:27])(=O)=[O:24]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([O:8][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:24])=[O:22])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 58415206HCID 58415206, compound

Product 1

HCID 60155357HCID 60155357, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound (8) (3.69 g, 14.9 mmol) and triethylamine (4.13 mL, 29.7 mmol) in dry dichloromethane, (CF3SO2)2O (2.93 mL, 17.8 mmol) was added dropwise at 0° C. After completion of the dropwise addition, the mixture was stirred at room temperature for 12 hours. The organic layer was washed sequentially with a 1M aqueous solution (90 mL) of hydrochloric acid, a 1M aqueous solution of sodium hydroxide (90 mL), and saline (90 mL), and dried (over sodium sulfate). The solvent was then distilled off. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (10:1) solution to give 5.44 g (96%) of compound (18) of interest as clear yellow liquid matter.

Workup

  1. additionAfter completion of the dropwise addition
  2. washThe organic layer was washed sequentially with a 1M aqueous solution (90 mL) of hydrochloric acid
  3. dry with materiala 1M aqueous solution of sodium hydroxide (90 mL), and saline (90 mL), and dried (over sodium sulfate)
  4. distillationThe solvent was then distilled off
  5. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (10:1) solution

Sources & evidence

ORD record
ord-3ad06f5ca111419890ae0a8170cea48d
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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