Dicyclohexylcarbodiimide → HCID 23085455, compound

HRID 1670404Notes

Reaction equation

HRID 1670404 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([OH:5])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.[Br:38][CH2:39][CH2:40]O>ClCCl>[CH3:1][C:2]([CH3:22])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([O:5][CH2:40][CH2:39][Br:38])=[O:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 108982-BromoethanolHCID 142760692,2-Dimethyloctadecanoic acid

Product 1

HCID 23085455HCID 23085455, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (1.6 mmol) of 2,2-Dimethyl-octadecanoic acid (Roth, Bruce D. et al., J. Med. Chem. 1992, 35(9), 1609-17) were dissolved in anhydrous dichloromethane (10 ml), and 350 mg (1.8 mmol) of dicyclohexylcarbodiimide (DCC), and 140 μl (2 mmol) of 2-bromoethanol were added thereto, followed by stirring of the mixture at room temperature overnight. The reaction mixture was purified using a silica gel column (elution by hexane-ethyl acetate (7:1) solvent mixture) to obtain 230 mg of 2-(2,2-dimethyloctadecanoyloxy)ethyl bromide to be used below.

Workup

  1. customThe reaction mixture was purified
  2. washa silica gel column (elution by hexane-ethyl acetate (7:1) solvent mixture)

Sources & evidence

ORD record
ord-96900058b68344bcb5410ebf24b7006d
Source dataset
uspto-grants-2011_08
Patent number
US07994152B2

Reaction notes

Loading…