Hydrochloric Acid → HCID 67417807, compound

HRID 2406026Notes

Reaction equation

HRID 2406026 reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:20]([C:32]#[N:33])[CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+].[ClH:51]>C(O)C.O1CCOCC1>[ClH:51].[NH2:7][C:8]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:20]([C:32]#[N:33])[CH:19]=1)([CH2:13][OH:12])[CH2:9][OH:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 57704560HCID 57704560, compound

Product 1

HCID 67417807HCID 67417807, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 5-1 (255 mg) was dissolved in ethanol (2 ml), p-toluenesulfonic acid (19 mg) was added, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give an oil. To the oil was added dioxane containing hydrogen chloride (4 mol/l), and the mixture was stirred at room temperature for 3 hr. The precipitate was collected by filtration and dried to give the object product (45 mg) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  6. customto give an oil
  7. stirringthe mixture was stirred at room temperature for 3 hr
  8. filtrationThe precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-70743a64a17a4405be852f952e3ebb91
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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