Triethylamine → HCID 54116100, compound

HRID 488302Notes

Reaction equation

HRID 488302 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([C:29](=[O:33])[C:30]([OH:32])=O)[CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(Cl)(=O)C(Cl)=O.[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>C(Cl)Cl.CN(C=O)C>[CH2:45]([O:44][C:42](=[O:43])[CH2:41][N:40]([C:30](=[O:32])[C:29]([C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:13]=1)=[O:33])[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH3:46]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80502Diethyl iminodiacetateHCID 19091779HCID 19091779, compound

Product 1

HCID 54116100HCID 54116100, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g (2.16 mmol) of 3,5-bis(decyloxy)-alpha-oxobenzeneacetic acid in 50 ml of anhydrous methylene chloride and 2 drops of DMF stirred in an ice bath was added 0.94 ml (10.8 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 an ice bath cooled solution of 0.6 ml (3.2 mmol) of diethyl iminodiacetate and 0.6 ml (4.3 mmol) of triethylamine in 10 ml of methylene chloride. After stirring in the ice bath for 30 minutes and at room temperature for 18 hours, the reaction mixture was washed with NaHCO3, dried and concentrated at reduced pressure to an oil which was purified by chromatography on 25 g of 230-400 mesh silica gel using 20% ethyl acetate-hexane to give 1.2 g (91% yield) of N-[[3,5-bis(decyloxy)phenyl]-1,2-dioxoethyl]-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester as an oil. The nmr and mass spectra served to confirm the structure.

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 an ice bath
  5. washthe reaction mixture was washed with NaHCO3
  6. customdried
  7. concentrationconcentrated at reduced pressure to an oil which
  8. customwas purified by chromatography on 25 g of 230-400 mesh silica gel using 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-c67e5c5dcaf54029a7142596d1c4a363
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…