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

HRID 499486ノート

反応式

HRID 499486 の反応式
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=[CH:5][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>[O:27]=[C:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[S:22][C:1]([C:3]2[N:8]=[C:7]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[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 22939284tert-butyl N-[2-(6-cyanopyridin-2-yl)ethyl]carbamate

生成物 1

HCID 59750335tert-Butyl 2-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethylcarbamate収率 64.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

tert-Butyl 2-(6-cyano-2-pyridyl)ethylcarbamate (2.0 g, 8.1 mmol) and methyl thiosalicylate (2.0 g, 12 mmol) were dissolved in toluene (10 ml), and triethylamine (5.0 ml, 36 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 (3:2, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (2.0 g, 64%) as white crystals.

後処理

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

出典と根拠

ORDレコード
ord-a680efa955444bcf9c364dfcec3ba599
出典データセット
uspto-grants-2010_08
特許番号
US07767665B2

反応ノート

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