Trifluoroacetic acid → HCID 22842608, compound

HRID 2371503Notes

Reaction equation

HRID 2371503 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][C@H:18]2[O:23]C(C)(C)[O:21][C@@H:20]([CH2:26][C:27]([O:29]C(C)(C)C)=O)[CH2:19]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(#N)C.C(Cl)Cl>C(Cl)Cl>[C:12]([C:9]1[CH:8]=[C:7]([S:16][CH2:17][C@H:18]2[O:23][C:27](=[O:29])[CH2:26][C@H:20]([OH:21])[CH2:19]2)[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:14])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15042010HCID 15042010, compoundHCID 21877088Acetonitrile methylene chloride

Product 1

HCID 22842608HCID 22842608, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 6.5 ml of anhydrous methylene chloride was dissolved 0.647 g (1.346 mmol) of tert-butyl [(4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-2,2-dimethyl-1,3-dioxane-4-yl]acetate. Thereto was added dropwise 1.3 ml of trifluoroacetic acid with cooling with ice and stirred for a half hour at the same temperature, further stirred for 2 hours at room temperature. The reaction solution was distilled away under reduced pressure. To the residue was added toluene, and again the mixture was distilled away under reduced pressure. After repeating such procedure twice, the obtained residue was purified by subjecting to silica gel column chromatography [eluent: acetonitrile-methylene chloride (1:9 to 1:4)]to give 0.396 g of (4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-4-hydroxytetrahydropyrane-2-one as crystals (yield: 83%). The desired compound was recrystallized from hexane.

Workup

  1. temperaturewith cooling with ice
  2. stirringfurther stirred for 2 hours at room temperature
  3. distillationThe reaction solution was distilled away under reduced pressure
  4. additionTo the residue was added toluene
  5. distillationagain the mixture was distilled away under reduced pressure
  6. customthe obtained residue was purified

Sources & evidence

ORD record
ord-317e87feed8e4ad0beec875047eb8b38
Source dataset
uspto-grants-1992_03
Patent number
US05093363

Reaction notes

Loading…