Methanol → Methyl (3S)-2-[(4-chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249067ノート

反応式

HRID 1249067 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][S:7][C:8]([N:10]2[C@H:22]([C:23]([OH:25])=[O:24])[CH2:21][C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:12]=3[CH2:11]2)=[S:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:32]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][S:7][C:8]([N:10]2[C@H:22]([C:23]([O:25][CH3:32])=[O:24])[CH2:21][C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:12]=3[CH2:11]2)=[S:9])=[CH:26][CH:27]=1

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 13561935(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

生成物 1

HCID 13561998Methyl (3S)-2-[(4-chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate収率 50%

実験手順

(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2.08 g) is dissolved in methanol (30 ml) and thereto is added dropwise thionyl chloride (0.94 ml) at -20° C. The mixture is stirred at 50°-60° C. for 5 hours and then distilled to remove the solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried, treated with active carbon and distilled to remove the solvent. The residue is recrystallized from ethyl acetate-n-hexane to give the title compound (1.08 g, 50%) as colorless needles, mp 181°-182° C. (decomp.).

後処理

  1. distillationdistilled
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed with water
  5. customdried
  6. additiontreated with active carbon
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-b938b2a1cc6c4befb1dec8ad01b397c6
出典データセット
uspto-grants-1986_12
特許番号
US04628057

反応ノート

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