p-Toluenesulfonic acid → HCID 69058271, compound

HRID 1727231Notes

Reaction equation

HRID 1727231 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15]C(C)(C)[O:17][C@:13]32[C@H:8]([C@H:9]([C:21]([CH3:25])=[C:22]([F:24])[F:23])[CH2:10][CH2:11][C@@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:26])(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([O:4][C@@H:5]1[C:6]([CH3:26])=[CH:7][C@@H:8]2[C@@:13]([OH:17])([C@@H:12]([CH3:20])[CH2:11][CH2:10][C@H:9]2[C:21]([CH3:25])=[C:22]([F:24])[F:23])[C@H:14]1[OH:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69058077HCID 69058077, compound

Product 1

HCID 69058271HCID 69058271, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of (3aS,4R,6aS,7R,10S,10aS)-7-(2,2-difluoro-1-methylvinyl)-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 151, 400 mg) and para-toluenesulfonic acid in methanol (20 ml) was stirred at room temperature for 24 hours. The reaction mixture was quenched with excess aqueous sodium hydrogen carbonate, diluted with water and extracted with diethyl ether (2×). The combined organic phases were washed with concentrated aqueous sodium chloride, dried (Na2SO4) and evaporated. The solid residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (5:95 and then 10:90) to give the product as a white solid (195 mg).

Workup

  1. customThe reaction mixture was quenched with excess aqueous sodium hydrogen carbonate
  2. additiondiluted with water
  3. extractionextracted with diethyl ether (2×)
  4. washThe combined organic phases were washed with concentrated aqueous sodium chloride
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe solid residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (5:95

Sources & evidence

ORD record
ord-3300ec4d98e843a49de2cdeef3cb0659
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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