2,6-Lutidine → HCID 66776186, compound

HRID 1665836Notes

Reaction equation

HRID 1665836 reaction equation
[CH:1]1([C:6]2[C:15]3[C@@H:14]([OH:16])[CH2:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]=3[N:9]=[C:8]([CH:19]([CH3:21])[CH3:20])[C:7]=2[C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[O:23])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])(=O)=O.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Si:48]([O:16][C@H:14]1[CH2:13][C:12]([CH3:17])([CH3:18])[CH2:11][C:10]2[N:9]=[C:8]([CH:19]([CH3:21])[CH3:20])[C:7]([C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=3)=[O:23])=[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[C:15]1=2)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 59822021HCID 59822021, compound

Product 1

HCID 66776186HCID 66776186, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-18 °C

Procedure

Under argon, 3.65 g (7.95 mmol) of the compound from Example 3A are initially charged in 80 ml of dry toluene. At room temperature, 3.41 g (31.8 mmol, 4 eq.) of 2,6-lutidine are then added, and the mixture is cooled to −18° C. 3.65 ml (15.9 mmol, 2 eq.) of tert-butyldimethylsilyl trifluoromethanesulphonate are added dropwise to this solution. After 20 min, the reaction mixture is warmed to 0° C. and stirred at this temperature for a further 55 min. For work-up, saturated ammonium chloride solution (100 ml) is added and the mixture is, after warming to room temperature, extracted with ethyl acetate. The aqueous phase is extracted two more times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography (silica gel, mobile phase: isohexane/ethyl acetate 9:1).

Workup

  1. temperaturethe reaction mixture is warmed to 0° C.
  2. temperatureafter warming to room temperature
  3. extractionextracted with ethyl acetate
  4. extractionThe aqueous phase is extracted two more times with ethyl acetate
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by chromatography (silica gel, mobile phase: isohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-e7cfdefbbd094dec95787eb070b456f9
Source dataset
uspto-grants-2011_10
Patent number
US08039629B2

Reaction notes

Loading…