Triethylamine → 4-(2-Chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

HRID 1251

반응식

HRID 1251 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2Cl)[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH2:23][O:24][CH2:25][CH:26]=O)[NH:7][C:6]=1[CH3:28])=[O:4].[ClH:29].[OH:30][NH3+:31].C(N(CC)CC)C>CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:29])[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH2:23][O:24][CH2:25][CH:26]=[N:31][OH:30])[NH:7][C:6]=1[CH3:28])=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 22029257Hydroxyammonium hydrochlorideHCID 867521804-(2-Chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester

생성물 1

HCID 730780804-(2-Chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 4-(2-chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester (ID, 6.2 g), hydroxylammonium hydrochloride (1.27 g) and triethylamine (1.85 g) in methanol (100 mL) was stirred at room temperature for 6 h. Methanol was removed under reduced pressure and the residue was dissolved in ethyl acetate (200 mL) and water (200 mL). With vigorous stirring, the pH of the mixture was adjusted to 10 with aqueous 1N sodium hydroxide solution. After stirring for a further 15 min, the organic layer was collected, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was recristallized from ether and hexane to give the title compound IB (6.1 g). HRMS: calc. for C20 H23CIN2O6 422.1245 found 422.1248; m.p. 161.4°-162.2° C.; IR (KBr, cm-1): 3446, 3379, 1698, 1671, 1601.

후처리

  1. customMethanol was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. stirringAfter stirring for a further 15 min
  4. customthe organic layer was collected
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4264e1627523496cb0a0bc9ac274b94e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723618

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