Triethylamine → HCID 19091837, compound

HRID 488299Notes

Reaction equation

HRID 488299 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([C:26](=[O:30])[C:27]([OH:29])=O)[CH:23]=[CH:24][CH:25]=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:22]1[CH:23]=[CH:24][CH:25]=[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:21]=1)=[O:30])[CH3:43]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80502Diethyl iminodiacetateHCID 19091767HCID 19091767, compound

Product 1

HCID 19091837HCID 19091837, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g (2.4 mmol) of 3-(octadecyloxy)-alpha-oxobenzeneacetic acid in 50 ml of anhydrous methylene chloride and 2 drops of DMF stirred in an ice bath was added 1.1 ml (11.9 mmol) of oxalyl chloride. The cooling bath was removed and stirring was continued at room temperature for 2 hours. The solvent was removed at reduced pressure and the residual acid chloride was dissolved in 40 ml of anhydrous methylene chloride and added dropwise to a stirred, ice bath cooled solution of 0.6 ml (3.6 mmol) of diethyl iminodiacetate and 0.66 ml (4.8 mmol) of triethylamine in 10 ml of methylene chloride. The mixture was stirred for 30 minutes in the ice bath and then at room temperature for 19 hours when it was washed with NaHCO3 solution, dried and concentrated to an oil which was purified by chromatography on 35 g of 230-400 mesh silica gel using 20% ethyl acetate-hexane to give 1.3 g (93% yield, mp 27°-29°) of N-(2-ethoxy-2-oxoethyl)-N-[2-[3-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine ethyl ester.

Workup

  1. customThe cooling bath was removed
  2. customThe solvent was removed at reduced pressure
  3. dissolutionthe residual acid chloride was dissolved in 40 ml of anhydrous methylene chloride
  4. additionadded dropwise to a stirred, ice bath
  5. washat room temperature for 19 hours when it was washed with NaHCO3 solution
  6. customdried
  7. concentrationconcentrated to an oil which
  8. customwas purified by chromatography on 35 g of 230-400 mesh silica gel using 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-30c2ceae3ab640fc94f17d1b67412f1f
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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