Sulfuric Acid → HCID 59331307, compound

HRID 1882020Notes

Reaction equation

HRID 1882020 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:36]3[NH:40][C:39]([C:41]4[S:42][CH:43]=[CH:44][N:45]=4)=[CH:38][CH:37]=3)[CH2:14][C@H:15]3[CH2:35][CH2:34][C:17]4(O[C@H](C5C=CC=CC=5)[C@@H](C5C=CC=CC=5)[O:18]4)[CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:36]3[NH:40][C:39]([C:41]4[S:42][CH:43]=[CH:44][N:45]=4)=[CH:38][CH:37]=3)[CH2:14][C@H:15]3[CH2:35][CH2:34][C:17](=[O:18])[CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 59331321HCID 59331321, compound

Product 1

HCID 59331307HCID 59331307, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)-1,3-thiazole (0.100 g) in 1,4-dioxane (2 mL) was added 4.5M aqueous sulfuric acid solution (2 mL) at room temperature, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio), and recrystallized from diethyl ether-hexane to give the title compound (0.03 g, yield 43%) as colorless crystals. MS: 441 (MH+). melting point 165-167° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio)
  6. customrecrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-661aaf3ddd694004852239b70479c642
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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