Ammonia → 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]-ethoxy]hexanamide

HRID 845472Notes

Reaction equation

HRID 845472 reaction equation
[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1.C([N:30](CC)CC)C.ClC(OCC)=O.N>ClCCl>[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH2:30])=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 135902686-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid

Product 1

HCID 201311496-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]-ethoxy]hexanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acid (Example 1; 10 g, 0.027M) and triethylamine (3.0 g, 0.030 mol) in dry dichloromethane (100 ml) at -50° C. was treated dropwise with ethyl chloroformate (3.2 g, 0.029 mol). The solution was allowed to warm up to 0° C. over 0.5 hours, cooled back to -78° C. and treated with gaseous ammonia. The solution was allowed to warm up to room temperature over 6 hours and washed with an aqueous saturated solution of sodium hydrogen carbonate and dried (Na2CO3). The solvent was evaporated off under reduced pressure to give a residue which was purified by column chromatography (silica gel, ethyl acetate to 10% methanol in ethyl acetate) to give 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]-ethoxy]hexanamide as a pale yellow oil.

Workup

  1. temperaturecooled back to -78° C.
  2. temperatureto warm up to room temperature over 6 hours
  3. washwashed with an aqueous saturated solution of sodium hydrogen carbonate
  4. dry with materialdried (Na2CO3)
  5. customThe solvent was evaporated off under reduced pressure
  6. customto give a residue which
  7. customwas purified by column chromatography (silica gel, ethyl acetate to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-d9400aaa9df04f78b8dabf173e934016
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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