Ethanol hydrochloride → HCID 178454496, compound

HRID 963683Notes

Reaction equation

HRID 963683 reaction equation
[CH3:1][C:2](=[CH2:54])[C:3]([NH:5][C:6]1[N:7]=[C:8]([CH2:51][CH2:52][CH3:53])[N:9]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:10]=1[C:11]([O-:13])=[O:12])=[O:4].Cl.[CH2:56](O)[CH3:57]>>[CH3:1][C:2](=[CH2:54])[C:3]([NH:5][C:6]1[N:7]=[C:8]([CH2:51][CH2:52][CH3:53])[N:9]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:28][N:29]=[N:30][N:31]=3)=[CH:19][CH:20]=2)[C:10]=1[C:11]([O:13][CH2:56][CH3:57])=[O:12])=[O:4]

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 86752767HCID 86752767, compound

Product 1

HCID 178454496HCID 178454496, compoundYield 42%

Procedure

To 250 mg of ethyl ,4-[N-(2-methylacryloyl)amino]-2-n-propyl-1-[[2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylate was added 10 mL of 2N--HCl-ethanol (1:1) and the mixture was stirred at an external temperature of 90° C. for 4 hours. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (chloroform-methanol=20:1) and recrystallized from acetonitrile to provide 71 mg of ethyl 4-[N-(2-methylacryloyl)amino]-2-n-propyl-1-[[2'-(tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole-5-carboxylate (yield 42%).

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. customthe residue was purified by silica gel chromatography (chloroform-methanol=20:1)
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-08ba91f87e50415c8bec025aea0f0907
Source dataset
uspto-grants-1998_06
Patent number
US05763619

Reaction notes

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