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

HRID 748285ノート

反応式

HRID 748285 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24b71ff8dbc740feb17860698167b108
出典データセット
uspto-grants-2008_07
特許番号
US07399759B2

反応ノート

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