Triethylamine → ethyl 5-[[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethyl]amino]-5-oxopentanoate

HRID 1380124Notes

Reaction equation

HRID 1380124 reaction equation
Cl[C:2]([CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:3].[NH2:12][CH:13]([CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(N(CC)CC)C>ClCCl>[N:15]1([CH2:14][CH:13]([NH:12][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78881Ethyl 5-chloro-5-oxovalerateHCID 201311651-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

Product 1

HCID 20131172ethyl 5-[[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethyl]amino]-5-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 4-(chloroformyl)butyrate (0.714 g, 0.004 mol) in dichloromethane (5 ml) was added dropwise to a stirred solution of 1-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (Example 32c; 1.0 g, 0.0038 mol) and triethylamine (0.4 g, 0.004 mol) in dichloromethane (20 ml) at room temperature. The solution was stirred for 12 hours, washed with an aqueous saturated solution of ammonium chloride and dried (Na2SO4). The solvent was evaporated off under reduced pressure and the crude product was purified by column chromatography (silica gel, 2% ethanol in chloroform) to give ethyl 5-[[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethyl]amino]-5-oxopentanoate as a pale-yellow oil.

Workup

  1. washwashed with an aqueous saturated solution of ammonium chloride
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe crude product was purified by column chromatography (silica gel, 2% ethanol in chloroform)

Sources & evidence

ORD record
ord-8c3f9233a06f4700877ba2e0837bd668
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

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