Triethylamine → HCID 19091889, compound

HRID 488291Notes

Reaction equation

HRID 488291 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:24]([CH:28]=1)[C:25](O)=[O:26])[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].[NH:37]([CH2:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40].C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[C:54]1([CH2:53][O:52][C:50](=[O:51])[CH2:49][N:37]([C:25](=[O:26])[C:24]2[CH:28]=[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]=[CH:22][C:23]=2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:38][C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10662990HCID 10662990, compoundHCID 19091843HCID 19091843, compound

Product 1

HCID 19091889HCID 19091889, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 1.0 g (2.0 mmol) of 5-(octadecyloxy)-2-(phenylmethoxy)benzoic acid in 5 ml of thionyl chloride was heated to reflux for 1 hour and then concentrated at reduced pressure. The resultant acid chloride was dissolved in 30 ml of anhydrous THF and added dropwise to a stirred mixture of 0.785 g (2.5 mmol) of dibenzyl iminodiacetate and 0.85 ml (6.1 mmol) of triethylamine in 10 ml of THF. The reaction mixture was stirred at room temperature for 20 hours and the solvent was removed at reduced pressure. The product was purified by HPLC using 5% ethyl acetate-hexane to give 0.70 g (44% yield) of N-[5-(octadecyloxy)-2-(phenylmethoxy) benzoyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester as an oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated at reduced pressure
  4. dissolutionThe resultant acid chloride was dissolved in 30 ml of anhydrous THF
  5. customthe solvent was removed at reduced pressure
  6. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-f211a5dd056a4a63850d3c057b50c61c
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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