Hydrochloric Acid → HCID 68466223, compound

HRID 502983Notes

Reaction equation

HRID 502983 reaction equation
Cl.C1COCC1.CC1(C)[O:32][CH2:31][C:11]2([CH2:14][C:13]([C:20]3[N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:23]4=[N:22][N:21]=3)([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[CH2:12]2)[CH2:10][O:9]1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[N:22]1[N:21]=[C:20]([C:13]2([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][C:11]([CH2:31][OH:32])([CH2:10][OH:9])[CH2:14]2)[N:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:23]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 68465851HCID 68465851, compound

Product 1

HCID 68466223HCID 68466223, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1M Hydrochloric acid was added to a THF (10 ml) solution of 3-[7,7-dimethyl-2-(2-thienyl)-6,8-dioxaspiro[3,5]non-2-yl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (2270 mg) and the whole was stirred at room temperature for 30 minutes. The reaction solution and chloroform were added to a saturated aqueous sodium hydrogen carbonate solution and then the organic layer was separated. Furthermore, the organic layer washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=9:1) to obtain 1862 mg of [3-(5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutane-1,1-diyl]dimethanol (colorless solid).

Workup

  1. customthe organic layer was separated
  2. washFurthermore, the organic layer washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-110ed3c99017470db4446c51082a0ab0
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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