Sodium Bicarbonate → HCID 68554937, compound

HRID 1854674Notes

Reaction equation

HRID 1854674 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](=[O:30])[CH2:18][C:19](=[O:29])/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>O1CCCC1>[NH2:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[C:17](=[O:30])[CH2:18][C:19](=[O:29])/[CH:20]=[CH:21]/[C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 68551182HCID 68551182, compound

Product 1

HCID 68554937HCID 68554937, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1E,6E)-1-[4-(tert-butoxycarbonylamino)phenyl]-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione (22 mg, 54 μmol, synthesized in Example 278) in 1 mL of tetrahydrofuran was added 2 mL of 4N HCl/dioxane at room temperature. After being stirred at the same temperature for 1 h, the reaction mixture was neutralized with saturated NaHCO3 aqueous solution. The mixture was extracted with chloroform, and the organic layer was dried over Na2SO4. After filtration, the filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 50/50) to obtain the title compound as a solid (5.8 mg, 35%) having the following characteristics.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 50/50)

Sources & evidence

ORD record
ord-73ca935f8be442088bcffe42c9b567e6
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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