Ethyl Acetate → (E)-methyl 4-(2-(2-(tert-butoxycarbonyl)ethoxy)ethylamino)-4-oxobut-2-enoate

HRID 926904Notes

Reaction equation

HRID 926904 reaction equation
NCCOCCN[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[C:15]([O:22][CH3:23])(=[O:21])/[CH:16]=[CH:17]/[C:18]([O-:20])=O.CCN=C=NC[CH2:30][CH2:31][N:32](C)C.[CH3:35][CH2:36][O:37]C(C)=O>CC#N>[C:10]([O:9][C:8]([CH2:35][CH2:36][O:37][CH2:30][CH2:31][NH:32][C:18](=[O:20])/[CH:17]=[CH:16]/[C:15]([O:22][CH3:23])=[O:21])=[O:14])([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamateHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

Product 1

HCID 86655429(E)-methyl 4-(2-(2-(tert-butoxycarbonyl)ethoxy)ethylamino)-4-oxobut-2-enoateYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (1.0 g, 4.90 mmol) was then taken up in 20 mL of CH3CN along with mono methyl fumarate (637 mg, 4.90 mmol) and EDCI (1.7 g, 5.39 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3, brine, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (9:1 CH2Cl2/MeOH) to afford 1.0 g of (E)-methyl 4-(2-(2-(tert-butoxycarbonyl)ethoxy)ethylamino)-4-oxobut-2-enoate (64% yield). MS (EI) called for C14H24 N2O6: 316.16; found 317 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with saturated aqueous NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-a0ff1f8d2e6940408a9a4abbf4ed772f
Source dataset
uspto-grants-2016_03
Patent number
US09289503B2

Reaction notes

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