Triethylamine → 2-Ethoxy-3-[4-(2-heptanoylaminoethoxy)phenyl]propionic acid ethyl ester

HRID 1744457Notes

Reaction equation

HRID 1744457 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH2:16])=[CH:9][CH:8]=1)[CH3:2].C(N(CC)CC)C.[C:28](Cl)(=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][C:28](=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17313Heptanoyl chlorideHCID 108589313-[4-(2-Aminoethoxy)phenyl]-2-ethoxypropionic acid ethyl ester

Product 1

HCID 696256202-Ethoxy-3-[4-(2-heptanoylaminoethoxy)phenyl]propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound obtained in Step c (55 mg) was dissolved in methylene chloride (2 ml), added with triethylamine (56 μl and added with n-heptanoyl chloride (39 μl, produced by Tokyo Kasei Kogyo). The reaction mixture was stirred at room temperature for 30 minutes, diluted with methylene chloride, washed with saturated aqueous sodium hydrogencarbonate, dried over magnesium sulfate and concentrated. The resulting residue was applied on a silica gel column and eluted with hexane/ethyl acetate (3:2) to obtain the title compound (47.3 mg).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. washeluted with hexane/ethyl acetate (3:2)

Sources & evidence

ORD record
ord-d9a50fd1dc774604a1040cd4d9d9f8fc
Source dataset
uspto-grants-2006_03
Patent number
US07015345B2

Reaction notes

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