Reaction #710537

ord-ebe0b431102c4166816d2cd5819021d0

Reaction equation

COC(=O)/C=C/C(=O)[O-]
Monomethyl fumarate
CCN=C=NCCCN(C)C.Cl
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
OCCCCN1CCOCC1
4-Morpholin-4-yl-butan-1-ol
→
COC(=O)/C=C/C(=O)OCCCCN1CCOCC1
title compound
COC(=O)/C=C/C(=O)OCCCCN1CCOCC1
Methyl 4-morpholin-4-ylbutyl (2E)but-2-ene-1,4-dioate

Reactants

COC(=O)/C=C/C(=O)[O-]
Monomethyl fumarate
CCN=C=NCCCN(C)C.Cl
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
—
4-N,N-dimethylaminopyridine
—
carboxylic acid
OCCCCN1CCOCC1
4-Morpholin-4-yl-butan-1-ol

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherAfter the completion of the reaction

Procedure

Monomethyl fumarate (MMF) was reacted with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC) (1.2 eq) in dichloromethane (DCM) at ca. 0° C. 4-Morpholin-4-yl-butan-1-ol (1 eq) and 4-N,N-dimethylaminopyridine (DMAP) (catalytic amount) were added to the activated carboxylic acid. After the completion of the reaction, followed by the work-up of the reaction mixture, the title compound was isolated as a viscous-oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09302977B2uspto-grants-2016_04