Triethylamine → N-(2-ethoxy-2-oxoethyl)-N-[3-[3-(phenoxy)propoxy]-5-(octadecyloxy)benzoyl]glycine ethyl ester

HRID 488259Notes

Reaction equation

HRID 488259 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:28]=1)[C:23]([OH:25])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH:40]([CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43].C(N(CC)CC)C>S(Cl)(Cl)=O.C1(C)C=CC=CC=1.C1COCC1>[CH2:45]([O:44][C:42](=[O:43])[CH2:41][N:40]([CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:23](=[O:25])[C:22]1[CH:21]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:28]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:26]=1)[CH3:46]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 80502Diethyl iminodiacetateHCID 152328343-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid

Product 1

HCID 19091821N-(2-ethoxy-2-oxoethyl)-N-[3-[3-(phenoxy)propoxy]-5-(octadecyloxy)benzoyl]glycine ethyl esterYield 91.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 1.0 g (1.85 mmol) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid in 10 ml of thionyl chloride and 4 ml of toluene was stirred at reflux for 4.5 hours. The mixture was concentrated at reduced pressure, the residual acid chloride was dissolved in 10 ml of anhydrous THF and added dropwise to a solution of 0.44 g (2.3 mmol) of diethyl iminodiacetate and 0.8 ml (5.8 mmol) of triethylamine in 20 ml of THF with stirring. The reaction mixture was stirred at room temperature for 16 hours and then was concentrated at reduced pressure to yield an oil. Purification by HPLC using 20% ethyl acetate-hexane to give 1.2 g of N-(2-ethoxy-2-oxoethyl)-N-[3-[3-(phenoxy)propoxyl]-5-(octadecyloxy)benzoyl] glycine ethyl ester as an oil.

Workup

  1. temperatureat reflux for 4.5 hours
  2. concentrationThe mixture was concentrated at reduced pressure
  3. dissolutionthe residual acid chloride was dissolved in 10 ml of anhydrous THF
  4. stirringThe reaction mixture was stirred at room temperature for 16 hours
  5. concentrationwas concentrated at reduced pressure
  6. customto yield an oil
  7. customPurification by HPLC

Sources & evidence

ORD record
ord-c2adc12668c24045beb210a6f18179b9
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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