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

HRID 869784

反応式

HRID 869784 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2188da8053ff4171b02b559fec2ef915
出典データセット
uspto-grants-2015_03
特許番号
US08969354B2

関連ノート

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