2-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoate → 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1087643노트

반응식

HRID 1087643 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH:7]=[C:8]([P:12]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:9]([CH3:11])=O)([O-:3])=[O:2].[CH2:22]([N:29]([CH2:31][CH2:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37])[CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[CH3:37][C:36]1[NH:38][C:9]([CH3:11])=[C:8]([P:12]2(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:7]([C:6]2[CH:19]=[CH:20][CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:35]=1[C:34]([O:33][CH2:32][CH2:31][N:29]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:30])=[O:39]

참가 물질

4

반응물 2

HCID 125291882-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoateHCID 540679512-(1-(3-Nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane

생성물 1

HCID 136045572-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate수율 59.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 3.11 grams of 2-(1-(3-nitrobenzylidene)-acetonyl)-2-oxo-1,3,2-dioxaphosphorinane and 2.48 grams of 2 -(N-benzyl-N-methylamino)ethyl3-aminocrotonate was dissolved in 30 ml of isopropanol and the mixture was heated to reflux for eight hours. The reaction solution was concentrated in vacuo and the residue was purified by subjecting to a column chromatography (silica gel, n-hexane-ethyl acetate). The resulting pale yellow oil (3.8 grams) was crystallized with ether and recrystallized from a mixture of ethyl acetate and ether to give 3.2 grams of 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan- 2-yl)-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, m.p. 139°-40° C.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for eight hours
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customthe residue was purified
  5. customThe resulting pale yellow oil (3.8 grams) was crystallized with ether
  6. customrecrystallized from a mixture of ethyl acetate and ether

출처 및 근거

ORD 기록
ord-cebe0f14f78043ea8b0bbe32e27dc24b
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036059

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