Dicyclohexylamine → (2E)-3-({[(Methylethyl)oxycarbonyloxy]ethyl}oxycarbonyl)prop-2-enoic acid

HRID 1626077Notes

Reaction equation

HRID 1626077 reaction equation
[CH3:1][CH:2]([O:4][C:5]([O:7][CH2:8][CH2:9]Cl)=[O:6])[CH3:3].C1CCC(NC2CCCCC2)CC1.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28]>CN1CCCC1=O>[CH3:1][CH:2]([O:4][C:5]([O:7][CH2:8][CH2:9][O:29][C:27](/[CH:26]=[CH:25]/[C:24]([OH:31])=[O:30])=[O:28])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 444972Fumaric AcidHCID 197651192-Chloroethyl propan-2-yl carbonate

Product 1

HCID 86639361(2E)-3-({[(Methylethyl)oxycarbonyloxy]ethyl}oxycarbonyl)prop-2-enoic acidYield 10%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, chloroethyl (methylethoxy)formate (0.25 g, 1.50 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 (0.030 g, 10% yield) of the title compound (50) as a white, waxy, semi-solid. 1H NMR (CD3CN, 400 MHz): δ 6.86 (q, J=5.6 Hz, 1H), 6.81 (d, J=16.0 Hz, 1H), 6.73 (d, J=16.0 Hz, 1H), 2.57-2.50 (heptet, J=7.2 Hz, 1H), 1.48 (d, J=5.6 Hz, 3H), 1.13 (m, 6H). MS (ESI): m/z=244.99 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-d3efcdb6b84347829e660dd24c2704a7
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Reaction notes

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