Triethylamine → N-(2-methoxy-2-oxoethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine methyl ester

HRID 488280Notes

Reaction equation

HRID 488280 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19]([OH:21])=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][CH3:14].S(Cl)(Cl)=O.[NH:44]([CH2:50][C:51]([O:53][CH3:54])=[O:52])[CH2:45][C:46]([O:48][CH3:49])=[O:47].C(N(CC)CC)C>C(Cl)Cl>[CH3:54][O:53][C:51](=[O:52])[CH2:50][N:44]([CH2:45][C:46]([O:48][CH3:49])=[O:47])[C:19](=[O:21])[C:18]1[CH:22]=[CH:23][C:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:16]([O:15][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][CH3:14])[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 428827Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetateHCID 190162583,4-Bis(tetradecyloxy)benzoic acid

Product 1

HCID 19091769N-(2-methoxy-2-oxoethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.8 g (1.46 mmol) of 3,4-bis(tetradecyloxy)benzoic acid and 20 ml of thionyl chloride was stirred at reflux for 3 hours. The excess thionyl chloride was removed at reduced pressure and the resultant acid chloride was dissolved in 10 ml of methylene chloride and 10 ml of anhydrous THF. This solution was added dropwise to a stirred, ice cooled mixture of 0.3 ml (1.86 mmol) of dimethyl iminodiacetate and 0.41 ml (2.9 mmol) of triethylamine in 10 ml of anhydrous methylene chloride. The cooling bath was removed after 30 minutes and the mixture was left at room temperature for 18 hours. The solvents were removed at reduced pressure and the residue was extracted with ethyl acetate. The extract was washed successively with 1N HCl, with NaHCO3 solution, dried and concentrated. Crystallization from ethyl acetate-hexane gave 0.905 g (90% yield, mp 70°-71°) of N-(2-methoxy-2-oxoethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine methyl ester.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe excess thionyl chloride was removed at reduced pressure
  3. dissolutionthe resultant acid chloride was dissolved in 10 ml of methylene chloride
  4. additionThis solution was added dropwise to a stirred, ice
  5. temperaturecooled
  6. customThe cooling bath was removed after 30 minutes
  7. customThe solvents were removed at reduced pressure
  8. extractionthe residue was extracted with ethyl acetate
  9. washThe extract was washed successively with 1N HCl, with NaHCO3 solution
  10. customdried
  11. concentrationconcentrated
  12. customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9cdc971561734d17acbe37637068c7f9
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…