Dicyclohexylcarbodiimide → HCID 11371886, compound

HRID 2090078Notes

Reaction equation

HRID 2090078 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5](=[O:10])[C:6]([Br:9])([CH3:8])[CH3:7].[O:11]=[C:12]1[CH:16]=[CH:15][C:14](=[O:17])[N:13]1[CH2:18][CH2:19][C:20](O)=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[O:11]=[C:12]1[CH:16]=[CH:15][C:14](=[O:17])[N:13]1[CH2:18][CH2:19][C:20]([O:1][CH2:2][CH2:3][O:4][C:5](=[O:10])[C:6]([Br:9])([CH3:8])[CH3:7])=[O:21]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5736213-Maleimidopropionic acidHCID 114812562-HYDROXYETHYL 2-BROMOISOBUTYRATE2×

Product 1

HCID 11371886HCID 11371886, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-Hydroxyethyl-2-bromo-2-methylpropionate (initiator 9) (0.187 g, 0.887 mmol) and 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-propionic acid (0.300 g, 1.77 mmol) were dissolved in dichloromethane (10 ml) under nitrogen in a 25 ml round-bottomed flask. Then N,N′-Dicyclohexylcarbodiimide (DCC) (0.366 g, 1.77 mmol) was added to the solution. After one day at room temperature, very low conversion was observed and 0.5 ml (9.50×10−3 mmol) of a solution of 4-dimethylaminopyridine (DMAP) in dichloromethane (Conc.DMAP=19 mmol/l) was added. Total conversion was then achieved in 12 hours and the solvent was removed under reduced pressure. The solid residue was extracted with 3×50 ml of petroleum ether and the petroleum ether was removed by evaporation under vacuum in order to isolate a colourless oil (0.270 g, 0.745 mmol, 84%). The pale pink residue was extracted with 3×50 ml of diethylether, but TLC (CH2Cl2/AcOEt 9:1) revealed that only traces of the ester were present. An analytical pure sample was obtained by flash chromatography (cc, SiO2, Pet. Ether/Et2O 3:1).

Workup

  1. waitTotal conversion was then achieved in 12 hours
  2. customthe solvent was removed under reduced pressure
  3. extractionThe solid residue was extracted with 3×50 ml of petroleum ether
  4. customthe petroleum ether was removed by evaporation under vacuum in order

Sources & evidence

ORD record
ord-579900ef91cc4336a1489150d7835a3f
Source dataset
uspto-grants-2013_05
Patent number
US08436104B2

Reaction notes

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