Triethylamine → 2-Chloromaleic acid

HRID 2046531

Reaction equation

HRID 2046531 reaction equation
C[N@+]1(CCC[O:32][C:33](/[C:35](/[Cl:70])=[CH:36]/[C:37]([O:39]CCC[N@+]2(C)[C@@H](C3C=C(OC)C(OC)=C(OC)C=3)C3C=C(OC)C(OC)=CC=3CC2)=[O:38])=[O:34])[C@H](CC2C=C(OC)C(OC)=C(OC)C=2)C2C(=CC(OC)=C(OC)C=2)CC1.Cl/C(=C\C([O-])=O)/C([O-])=O.C(N(CC)CC)C>C(#N)C>[Cl:70]/[C:35](=[CH:36]\[C:37]([OH:39])=[O:38])/[C:33]([OH:34])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10102486GantacuriumHCID 21982578HCID 21982578, compound

Product 1

HCID 52844882-Chloromaleic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Gantacurium, an asymmetrical chlorofumarate, was prepared in four chemical transformations from compound (XIIIB) using minor modifications of previously reported chemistry, see WO2005/041960. Isoquinolylalkanol compound (XIIIB) was condensed with trans-2,3-dichlorosuccinic anhydride and triethylamine in acetonitrile solvent to provide a monoester of chlorofumaric acid, which was then condensed with isoquinolylalkanol compound (XIIIC):

Sources & evidence

ORD record
ord-bfa23cbf96724e8aae7a97aca570a95b
Source dataset
uspto-grants-2013_11
Patent number
US08592451B2

Linked notes

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