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

HRID 869784

반응식

HRID 869784 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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) calcd for C14H24N2O6: 316.16. found: 317 (M+1).

후처리

  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)

출처 및 근거

ORD 기록
ord-2188da8053ff4171b02b559fec2ef915
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969354B2

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