Triethylamine → HCID 178440059, compound

HRID 1033609Notes

Reaction equation

HRID 1033609 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH2:48][CH2:49][CH3:50])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7]=1[C:8]([OH:10])=[O:9])[CH3:2].[C:51]([O:54][CH2:55]Cl)(=[O:53])[CH3:52].C(N(CC)CC)C>C1COCC1>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:48][CH2:49][CH3:50])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7]=1[C:8]([O:10][CH2:55][O:54][C:51](=[O:53])[CH3:52])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69366Chloromethyl acetateHCID 15228887HCID 15228887, compound

Product 1

HCID 178440059HCID 178440059, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.37 g of 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylic acid was dissolved in 5 mL THF and 0.5 g chloromethyl acetate and 0.5 mL triethylamine were added. The resulting solution was stirred overnight. The solvent was evaporated and the residue dissolved in methanol with 0.25 mL acetic acid and stirred 8 hours with 10 g silica gel. The mixture was evaporated and the residue on the gel was flash chromatographed with MeOH/CH2Cl2 (1:9) to provide 0.124 g of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol with 0.25 mL acetic acid
  3. stirringstirred 8 hours with 10 g silica gel
  4. customThe mixture was evaporated
  5. customchromatographed with MeOH/CH2Cl2 (1:9)

Sources & evidence

ORD record
ord-24c08999b21f4e38b72d180ad0f44c29
Source dataset
uspto-grants-1994_05
Patent number
US05310929

Reaction notes

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