Dicyclohexylcarbodiimide → 2-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl ester

HRID 638737Notes

Reaction equation

HRID 638737 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O[CH2:17][CH2:18][O:19][C:20](=[O:33])[CH:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([O:12][CH2:17][CH2:18][O:19][C:20](=[O:33])[CH:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[CH3:22])=[O:11])=[CH:14][CH:15]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 38051392-(4-Nitrophenoxy)propanoic acidHCID 592539752-(4-Nitrophenoxy)-propionic acid 2-hydroxy-ethyl ester

Product 1

HCID 592539622-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl esterYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(4-nitrophenoxy) propionic acid 47 (25 grams, 118.5 mmol) and 2-(4-nitrophenoxy)propionic acid 2-hydroxyethyl ester 48 ( 25 grams, 108 mmol) in anhydrous dichloromethane (625 ml) under nitrogen atm. was added dropwise a solution of 1,3-dicyclohexyl carbodiimide (40 g, 194 mmol) in anhydrous dichloro-methane (250 ml). The reaction mixture was stirred at room temperature for 8 hours. The solids were filtered off and dichloromethane distilled off to get crude 49. The crude 49 was purified by column chromatography on silica gel using hexane as eluant to get pure 49 (17 g, 35.1%) as a white powder.

Workup

  1. filtrationThe solids were filtered off
  2. distillationdichloromethane distilled off
  3. customto get crude 49
  4. customThe crude 49 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-542ef35583d5416aa027eeeac55df79f
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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