Fumaric Acid → HCID 86639360, compound

HRID 1626076Notes

Reaction equation

HRID 1626076 reaction equation
[CH3:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][CH2:7]Cl)=[O:4].[C:10]([OH:17])(=[O:16])/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14]>CN1CCCC1=O>[CH3:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][CH2:7][O:15][C:13](/[CH:12]=[CH:11]/[C:10]([OH:17])=[O:16])=[O:14])=[O:4]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 520648HCID 520648, compound

Product 1

HCID 86639360HCID 86639360, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, chloroethyl 2-methylpropanoate (0.24 g, 1.58 mmol) was reacted overnight with the pre-formed bis-dicyclohexylamine salt (DCHA) of fumaric acid (FA) (0.50 g, 1.26 mmol) in N-methylpyrrolidinone (NMP) at ca 100° C. The crude material was purified by mass-guided preparative HPLC to afford (0.035 g, 12% yield) of the title compound (49) as a white, waxy, semi-solid. 1H NMR (CD3CN, 400 MHz): δ 6.89-6.83 (q, J=5.6 Hz, 1H), 6.82-6.81 (d, J=16.0 Hz, 1H), 6.73-6.69 (d, J=16.0 Hz, 1H), 2.58-2.49 (heptet, J=6.8 Hz, 1H), 1.49-1.47 (d, J=5.6 Hz, 3H), 1.12 (d, J=7.2 Hz, 3H), 1.09 (d, J=6.8 Hz, 6H); MS (ESI): m/z=239.01 (M−H)−.

Workup

  1. customThe crude material was purified by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-ea3a354ca714413ca11988de133bed16
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Reaction notes

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