Triethylamine → N-(2-ethoxy-2-oxoethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine ethyl ester

HRID 488295Notes

Reaction equation

HRID 488295 reaction equation
[CH2:1]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:30])[C:27]([OH:29])=O)=[CH:22][CH:21]=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].C(Cl)(=O)C(Cl)=O.[NH:37]([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][N:37]([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:27](=[O:29])[C:26]([C:23]1[CH:22]=[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:25][CH:24]=1)=[O:30])[CH3:43]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80502Diethyl iminodiacetateHCID 190918534-(Octadecyloxy)-alpha-oxobenzeneacetic acid

Product 1

HCID 19091762N-(2-ethoxy-2-oxoethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine ethyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1.99 g (4.75 mmol) of 4-(octadecyloxy)-alpha-oxobenzeneacetic acid in 100 ml of methylene chloride and 3 drops of DMF stirred and cooled in an ice bath was added 2.1 ml (23.8 mmol) of oxalyl chloride. After 5 minutes the ice bath was removed and stirring was continued at room temperature for 1 hour. The reaction mixture was concentrated at reduced pressure and the resultant acid chloride was dissolved in 75 ml of anhydrous methylene chloride and added dropwise to an ice cooled solution of 1.25 ml (7.1 mmol) of diethyl iminodiacetate and 1.3 ml (9.5 mmol) of triethylamine in 25 ml of methylene chloride. The reaction mixture was stirred at room temperature for 17 hours and washed with NaHCO3 solution, dried and concentrated at reduced pressure. The resultant solid was recrystallized from methanol to give 2.4 g (86% yield, mp 63°-64°) of N-(2-ethoxy-2-oxoethyl)-N-[2-[4-(octadecyloxy)phenyl] -1,2-dioxoethyl]glycine ethyl ester.

Workup

  1. temperaturecooled in an ice bath
  2. customAfter 5 minutes the ice bath was removed
  3. stirringstirring
  4. concentrationThe reaction mixture was concentrated at reduced pressure
  5. dissolutionthe resultant acid chloride was dissolved in 75 ml of anhydrous methylene chloride
  6. stirringThe reaction mixture was stirred at room temperature for 17 hours
  7. washwashed with NaHCO3 solution
  8. customdried
  9. concentrationconcentrated at reduced pressure
  10. customThe resultant solid was recrystallized from methanol

Sources & evidence

ORD record
ord-bc2414b6c7a8465cae2bffb0b2e578dd
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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