Triethylamine → N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine ethyl ester

HRID 488284Notes

Reaction equation

HRID 488284 reaction equation
[C:1](Cl)(=[O:15])[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].[CH2:17]([O:19][C:20](=[O:39])[CH2:21][N:22]([C:29](=[O:38])[C:30]1[CH:35]=[C:34]([NH2:36])[CH:33]=[C:32]([NH2:37])[CH:31]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:18].C(N([CH2:45][CH3:46])CC)C>C1COCC1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:22]([CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:39])[C:29](=[O:38])[C:30]1[CH:35]=[C:34]([NH:36][C:1](=[O:15])[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:33]=[C:32]([NH:37][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:45][CH3:46])[CH:31]=1)[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66986Myristoyl chlorideHCID 19091775N-(3,5-diaminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester

Product 1

HCID 19091780N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine ethyl esterYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.9 ml (7 mmol) of myristoyl chloride in 10 ml of anhydrous THF was added dropwise to a stirred, ice cooled mixture of 1.0 g (3.09 mmol) of N-(3,5-diaminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester and 1.7 ml (12.4 mmol) of triethylamine in 20 ml of anhydrous THF. The reaction mixture was stirred in the cooling bath for 30 minutes and then at room temperature for 24 hours. The solvent was removed at reduced pressure and the residue was extracted with ethyl acetate. After washing with NaHCO3 solution, the dried extract was concentrated to an oil which was purified by chromatography on 120 g of silica gel using 40% ethyl acetate-hexane to give 2.1 g (91% yield) of N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine ethyl ester as a yellow oil. The nmr and mass spectra were consistent with the structure.

Workup

  1. temperaturecooled
  2. waitat room temperature for 24 hours
  3. customThe solvent was removed at reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washAfter washing with NaHCO3 solution
  6. extractionthe dried extract
  7. concentrationwas concentrated to an oil which
  8. customwas purified by chromatography on 120 g of silica gel using 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-7671299efba1488cada4f5c15394a02e
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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