Trifluoroacetic acid → HCID 86753808, compound

HRID 1417611Notes

Reaction equation

HRID 1417611 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:14]3[O:17][C@@:18]45[CH2:28][CH:27]=[CH:26][C:25]([CH3:30])([CH3:29])[C@@H:24]4[CH2:23][CH2:22][C@H:21]([CH3:31])[C@@:19]5([CH3:32])[CH2:20][C:13]=3[C:12]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=[CH:11][C:10]=2[C:9]1=[O:41])=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[Si:34]([O:33][C:12]1[C:13]2[CH2:20][C@:19]3([CH3:32])[C@@H:21]([CH3:31])[CH2:22][CH2:23][C@H:24]4[C:25]([CH3:30])([CH3:29])[CH:26]=[CH:27][CH2:28][C@@:18]34[O:17][C:14]=2[C:15]2[CH2:16][NH:8][C:9](=[O:41])[C:10]=2[CH:11]=1)([C:37]([CH3:40])([CH3:38])[CH3:39])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 86753809HCID 86753809, compound

Product 1

HCID 86753808HCID 86753808, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound (40b) (115 mg, 0.20 mmol) in 10 ml of dry dichloromethane were added 50 μl (0.46 mmol) of anisole and 32 μl (0.42 mmol) of trifluoroacetic acid under ice-cooling, and the mixture stirred for 4 hours at room temperature and allowed to stand over night. To the reaction mixture was added an aqueous saturated sodium hydrogen carbonate solution under ice-cooling, followed by extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (Merck, Lobar column, size A; n-hexane:ethyl acetate=3:2) to give 94 mg (98%) of Compound (41b).

Workup

  1. temperaturecooling
  2. waitto stand over night
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by a column chromatography (Merck, Lobar column, size A

Sources & evidence

ORD record
ord-1c51f8f84ee143eaa238a625d04008e2
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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