Triethylamine → tert-Butyl 3-[4-methyl-6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate

HRID 748263노트

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HRID 748263 반응식
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]([CH3:18])[CH:4]=1)#[N:2].[C:19](OC)(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[SH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:18][C:5]1[CH:4]=[C:3]([C:1]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19](=[O:27])[N:2]=2)[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:6]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939494tert-Butyl 3-(6-cyano-4-methyl-2-pyridyl)propanoate

생성물 1

HCID 22939440tert-Butyl 3-[4-methyl-6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate수율 55%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

tert-Butyl 3-(6-cyano-4-methyl-2-pyridyl)propanoate (0.72 g, 2.9 mmol) and methyl thiosalicylate (0.99 g, 5.9 mmol) were dissolved in toluene (4 ml), and triethylamine (2.0 ml, 14.3 mmol) was added thereto. The mixture was refluxed for 14 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:2, v/v) were collected, concentrated and recrystallized from ethyl acetate-hexane to give the titled compound (0.61 g, 54%) as white crystals.

후처리

  1. temperatureThe mixture was refluxed for 14 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate-hexane (1:2
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-8531ef0e34f041fe9759ebf10bd99c40
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399759B2

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