Isopropyl3-aminocrotonate → Isopropyl 2-methoxyethyl 4-(2-fluorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate

HRID 1978913노트

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HRID 1978913 반응식
[C:1]([C:4](=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])[C:5]([O:7][CH2:8][CH2:9][O:10][CH3:11])=[O:6])(=O)[CH3:2].[NH2:20][C:21]([CH3:29])=[CH:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24].C1(C)C=CC=CC=1.C(OCC)(=O)C>C(O)(C)C>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]1[C:4]([C:5]([O:7][CH2:8][CH2:9][O:10][CH3:11])=[O:6])=[C:1]([CH3:2])[NH:20][C:21]([CH3:29])=[C:22]1[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]

참가 물질

5

반응물 3

HCID 3271821Isopropyl3-aminocrotonateHCID 21584019Toluene ethylacetateHCID 599577782-Methoxyethyl 2-acetyl-3-(2-fluorophenyl)-2-propenoate

생성물 1

HCID 15295381Isopropyl 2-methoxyethyl 4-(2-fluorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate수율 48%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

4.0 g (about 15 mmol) of the compound from Example I are heated to reflux overnight in 100 ml of isopropanol with 2.2 g (15 mmol) of isopropyl 3-amino-2-butenoate. After thin-layer chromatographic checking (SiO2, toluene/ethyl acetate 5:1) shows complete conversion, the reaction mixture is concentrated, the residue is-taken up with toluene, the solution is concentrated again and the residue is then purified by filtration on silica gel (eluent: toluene/ethyl acetate 100:1-5:1). A crystallizing yellow oil is obtained, which is recrystallized from methanol at about −15° C. 2.8 g (48%) of the target compound are obtained.

후처리

  1. concentrationthe reaction mixture is concentrated
  2. concentrationthe residue is-taken up with toluene, the solution is concentrated again
  3. filtrationthe residue is then purified by filtration on silica gel (eluent: toluene/ethyl acetate 100:1-5:1)
  4. customA crystallizing yellow oil is obtained
  5. customwhich is recrystallized from methanol at about −15° C

출처 및 근거

ORD 기록
ord-9706872edf384106938727a6966dfb64
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239155B1

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