Triethylamine → tert-Butyl (6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methylcarbamate

HRID 499467노트

반응식

HRID 499467 반응식
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:18](OC)(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[SH:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:26]=[C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:1]([C:3]2[N:8]=[C:7]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamate

생성물 1

HCID 59750386tert-Butyl (6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methylcarbamate수율 72%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

tert-Butyl (6-cyano-2-pyridyl)methylcarbamate (1.6 g, 6.8 mmol) and methyl thiosalicylate (1.8 g, 10.9 mmol) were dissolved in toluene (6 ml), and triethylamine (3.0 ml, 21.5 mmol) was added thereto. The mixture was refluxed for 20 hrs. After cooling, the precipitates were collected by filtration and dissolved in chloroform. The solution was subjected to a silica gel column chromatography. The fractions eluted with chloroform-methanol (20:1, v/v) were collected, concentrated and recrystallized from hexane-chloroform to give the titled compound (1.8 g, 72%) as pale yellow crystals.

후처리

  1. temperatureThe mixture was refluxed for 20 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. dissolutiondissolved in chloroform
  5. washThe fractions eluted with chloroform-methanol (20:1
  6. customv/v) were collected
  7. concentrationconcentrated
  8. customrecrystallized from hexane-chloroform

출처 및 근거

ORD 기록
ord-199fe2f7b6134c3db314c233bfdbb1fe
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767665B2

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