Sodium Bicarbonate → HCID 178470243, compound

HRID 2259995Notes

Reaction equation

HRID 2259995 reaction equation
[CH3:1][C:2]1[C:3](/[C:16](/[CH3:34])=[CH:17]/[C:18]2[N:19]=[C:20]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:21](S(=O)(=O)N(C)C)[CH:22]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C([O-])(O)=O.[Na+]>Cl.CC(C)=O>[CH3:1][C:2]1[C:3](/[C:16](/[CH3:34])=[CH:17]/[C:18]2[N:19]=[C:20]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[NH:21][CH:22]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86749151ethyl (E)-4-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2-yl)propen-1-yl]-1-(N,N-dimethylsulfamoyl)-2-imidazolecarboxylate2×

Product 1

HCID 178470243HCID 178470243, compoundYield 186.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2-yl)propen-1-yl]-1-N, N-dimethylsulfamoyl-2-imidazolecarboxylate (Compound 4, 0.295 g, 0.605 mmol) was dissolved in a solution of 3M HCl (2.5 mL) and acetone (20 mL) at room temperature and the solution stirred for 30 min. The solution was neutralized with 5% aqueous NaHCO3 and the organic material was extracted with dichloromethane, washed with brine, dried (K2CO3) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate=3:2) to give the title compound as a light yellow solid (430 mg, 70%).

Workup

  1. extractionthe organic material was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-9e6362b2e7e940ed969531732a996c27
Source dataset
uspto-grants-1995_12
Patent number
US05475113

Reaction notes

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