Triethylamine → 3-{4-[2-(4-Benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester

HRID 987329Notes

Reaction equation

HRID 987329 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[CH3:2].[CH2:27]([N:34]=[C:35]=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:35](=[O:36])[NH:34][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:20][CH:21]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 54239207HCID 54239207, compound

Product 1

HCID 544876433-{4-[2-(4-Benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 26b) (0.36 g; 1.0 mmol) was dissolved in dry dichloromethane (25 ml) and benzylisocyanate (0.20 g; 0.185 ml; 1.5 mmol) was added followed by addition of triethylamine (0.22 ml; 1.5 mmol). The solution was stirred at room temperature for 3 hours. The dichloromethane phase was washed with diluted acid, sodium hydrogen carbonate and brine, dried with sodium sulfate and evaporated to give 0.4 g (81%) of crude 3-{4-[2-(4-benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester. The crude material was purified on preparative reversed phase HPLC using a gradient of acetonitrile-water-ammonium acetate as mobile phase. Fractions containing pure product were pooled and the acetonitrile removed in vacuum. The residue was dissolved in dichloromethane, washed with water, dried with sodium sulfate and evaporated to give 0.23 g (48%) of pure 3-{4-[2-(4-benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester

Workup

  1. washThe dichloromethane phase was washed
  2. additionwith diluted acid, sodium hydrogen carbonate and brine
  3. dry with materialdried with sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-7b1981fbcb404b98a8701a38c606ca13
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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