Trityl chloride → HCID 22012436, compound

HRID 1533277Notes

Reaction equation

HRID 1533277 reaction equation
C(OC([N:8]1[CH:12]=[C:11]([CH2:13][CH:14]([C:20]2[CH:25]=[CH:24][C:23]3[O:26][CH2:27][O:28][C:22]=3[CH:21]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:10]=[CH:9]1)=O)(C)(C)C.C(N(CC)CC)C.[C:36]1([C:42](Cl)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>FC(F)(F)C(O)=O.ClCCl>[C:36]1([C:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH:14]([C:20]3[CH:25]=[CH:24][C:23]4[O:26][CH2:27][O:28][C:22]=4[CH:21]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:10]=[CH:9]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 22012314HCID 22012314, compound

Product 1

HCID 22012436HCID 22012436, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 3-(1-tert-butoxycarbonylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate (633 mg) in trifluoroacetic acid (5 ml) was stirred at ambient temperature for 10 minutes. Trifluoroacetic acid was removed by evaporation and the residue was diluted with ethyl acetate followed by washing successively with saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of the solvents afforded a crude intermediate compound. To a solution of the above compound and triethylamine (214 mg) in dichloromethane (10 ml) was added portionwise triphenylmethyl chloride (545 mg) and the mixture was stirred at ambient temperature for 20 minutes. The resulting solution was washed successively with saturated ammonium chloride aqueous solution and saturated sodium bicarbonate aqueous solution. Drying, filtering and removal of the solvents afforded ethyl 3-[1-(triphenylmethyl)imidazol-4-yl]-2-(3,4-methylenedioxyphenyl)propionate (740 mg) as a slightly yellow oil.

Workup

  1. customTrifluoroacetic acid was removed by evaporation
  2. additionthe residue was diluted with ethyl acetate
  3. washby washing successively with saturated sodium bicarbonate aqueous solution and brine
  4. customDrying
  5. filtrationfiltering
  6. customremoval of the solvents
  7. customafforded a crude intermediate compound
  8. washThe resulting solution was washed successively with saturated ammonium chloride aqueous solution and saturated sodium bicarbonate aqueous solution
  9. customDrying
  10. filtrationfiltering
  11. customremoval of the solvents

Sources & evidence

ORD record
ord-461755862d8741bdbb5a6d59006db4e2
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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