N-(Methoxycarbonyl)maleimide

Off-White Cyrstalline Solid

To a solution of maleimide (6.35 g, 65.4 mmol) in ethyl acetate (120 niL) at 0 °C was added NMM (8.6 niL, 78.5 mmol), followed by methyl chloroformate (6.0 mL, 78.5 mmol). The reaction was stirred at 0 °C for 30 min and r.t. 1 h. The solid was filtered off and filtrate was concentrated. The residue was dissolved in methylene chloride and filtered through a silica gel plug and eluted with methylene chloride to remove the red color. After concentration, the solid was triturated with ethyl acetate and petroleum ether to give a white solid (9.0 g, 88percent yield).To a solution of maleimide 11 (3.0 g, 31 mmol) in ethyl acetate (120 mL) was added dropwise a solution of N-methyl morpholine (4.4 mL, 40.3 mmol) in ethyl acetate (15 mL) over 10 min at 0 Example 9:conversion of an amine to a maleimide moiety /V-(Methoxycarbonyl)maleimide (37) Methyl chloroformate (0.87 ml_, 11.3 mmol) was added slowly to a solution of maleimide (1.00 g, 10.3 mmol) and /V-methyl morpholine (1.24 ml_, 1 1.3 mmol) in EtOAc (80 ml_) at 0Methylchloroformate (4.4 niL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 niL of EtOAc at 0 The title compound was prepared using a modification of the method of Foley, et al., 2010 Biomol. Chem. 8:4601-4606).

Molecular Weight:155.11
XLogP3:-0.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:155.02185764
Monoisotopic Mass:155.02185764
Topological Polar Surface Area:63.7
Heavy Atom Count:11
Complexity:237
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes