Triethylamine → Ethyl 4-(2-(11-carbomethoxyundecanoylamino)phenoxy)butyrate

HRID 1003240Notes

Reaction equation

HRID 1003240 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C.[C:24]([O:39][CH3:40])(=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O-])=[O:36]>CCOCC>[C:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:36])([O:39][CH3:40])=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11816929Ethyl 4-(2-aminophenoxy)butanoateHCID 22672980Dodecanedioic acid, monomethyl ester

Product 1

HCID 18796179Ethyl 4-(2-(11-carbomethoxyundecanoylamino)phenoxy)butyrateYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred, ice-cold solution of 0.89 g (4.0 mM) amine (4) and dried triethylamine (1.2 mL) in dry ether (40 mL) is added dropwise over ca. 4 minutes a solution of acid chloride (7) (1.04 g, 4.6 mM) in 20 mL of dry ether. The resultant mixture is allowed to stir cold for 20 minutes, and then at room temperature overnight. After filtering off the triethylamine hydrochloride, the ether filtrate is concentrated in vacuo and the residue chromatographed on an 82 g silica gel column using 20% ethyl acetate/hexane as eluant to give 1.49 g (85%) of (8) as a waxy solid.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationAfter filtering off the triethylamine hydrochloride
  4. concentrationthe ether filtrate is concentrated in vacuo
  5. customthe residue chromatographed on an 82 g silica gel column

Sources & evidence

ORD record
ord-2578ee14247d41bdbcd3ef453315d198
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

Loading…