Dicyclohexylcarbodiimide → Ethyl 4-(2-(11-Bromoundecanoylamino)phenoxy)-butyrate

HRID 1290714Notes

Reaction equation

HRID 1290714 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].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([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:29]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1781211-Bromoundecanoic acidHCID 11816929Ethyl 4-(2-aminophenoxy)butanoate

Product 1

HCID 19603128Ethyl 4-(2-(11-Bromoundecanoylamino)phenoxy)-butyrateYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4) (2.60 g., 11 mM) and 11-bromoundecanoic acid (2.65 g., 10 mM) in anhydrous methylene chloride (90 mL) is added 4-(dimethylamino)pyridine (1.22 g., 10 mM) followed by N,N'-dicyclohexylcarbodiimide (2.3 g., 11 mM) (4×5 mL of methylenechloride rinses). Precipitation of dicyclohexylurea (DCU) begins within 4 minutes. When TLC analysis indicates the reaction is complete, the mixture is filtered, the filtrate concentrated in vacuo and the residue extracted with ether. The combined ether extracts are washed 1× with 1N hydrochloric acid, 1× saturated sodium chloride solution, dried (Na2SO4) and concentrated to a residue which is stirred, filtered, and concentrated alternately with ether and methylene chloride until all DCU is removed. Concentration of the final solution yields the title product (32) (2.35 g.) as an oil that goes readily to a waxy solid.

Workup

  1. customPrecipitation of dicyclohexylurea (DCU)
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. extractionthe residue extracted with ether
  5. washThe combined ether extracts are washed 1× with 1N hydrochloric acid, 1× saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to a residue which
  8. filtrationfiltered
  9. concentrationconcentrated alternately with ether and methylene chloride until all DCU
  10. customis removed

Sources & evidence

ORD record
ord-b10d6fcb4475433f919013e6dd75d2a3
Source dataset
uspto-grants-1998_05
Patent number
US05753641

Reaction notes

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