Methanol → HCID 178473644, compound

HRID 2260063Notes

Reaction equation

HRID 2260063 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH2:11][CH3:12])=[C:9]([C:13]([O:15][CH:16]([O:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:17])=[O:14])[N:8]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:37]4[N:41](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:40]=[N:39][N:38]=4)=[CH:27][CH:26]=3)[N:6]2[N:7]=1)[CH3:2].CO>C(O)(=O)C>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH2:11][CH3:12])=[C:9]([C:13]([O:15][CH:16]([O:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:17])=[O:14])[N:8]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:37]4[NH:41][N:40]=[N:39][N:38]=4)=[CH:27][CH:26]=3)[N:6]2[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 10843045HCID 10843045, compound

Product 1

HCID 178473644HCID 178473644, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture consisting of 5.64 g of 1-ethoxycarbonyloxyethyl 2,7-diethyl-5-[[2'-(N-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl]methyl]-5H-pyrazolo[1,5-b][1,2,4]triazole-6-carboxylate, 230 ml of methanol and 12 ml of acetic acid was heated under reflux for 3 hours. After removing the solvent by distillation under a reduced pressure, the resulting residue was subjected to silica gel column chromatography. Elution was conducted with a methanol-chloroform (1:19, v/v) mixed solvent to give 3.76 g of 1-ethoxycarbonyloxyethyl 2,7-diethyl-5-[[2'-(tetrazol-5-yl)biphenyl-4-yl]methyl]-5H-pyrazolo[1,5-b][1,2,4]triazole-6-carboxylate in the form of amorphous foamy material.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customAfter removing the solvent
  4. distillationby distillation under a reduced pressure
  5. washElution
  6. additionv/v) mixed solvent

Sources & evidence

ORD record
ord-de0c378832224c0fb8834280232f4ef8
Source dataset
uspto-grants-1995_12
Patent number
US05475114

Reaction notes

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