Thionyl Chloride → HCID 56629765、化合物

HRID 127578

反応式

HRID 127578 の反応式
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[NH:3]1.[C:16]([S:24][CH2:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(SCC(C)C(O)=O)(=O)C1C=CC=CC=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:16]([S:24][CH2:25][CH:26]([CH3:30])[C:27]([N:3]1[C@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 24386Thionyl ChlorideHCID 5694973-(Benzoylthio)-2-methylpropanoic acidHCID 2760578methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochlorideHCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioate

生成物 1

HCID 56629765HCID 56629765、化合物収率 80.5%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8471Triethylamine溶媒

実験手順

5.69 g of methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride are suspended in 50 ml of chloroform, and 5.6 g of triethylamine are added thereto under ice-cooling and stirring. 3-benzoylthio-2-methylpropionyl chloride (which is prepared by heating a mixture of 5.6 g of 3-benzoylthio-2-methyl-propionic acid and 6 ml of thionyl chloride at 60° C. for 2 hours, followed by distillation thereof to remove the excess of thionyl chloride) is dissolved in 10 ml of tetrahydrofuran, and said tetrahydrofuran solution is added dropwise to the suspension obtained above. After the mixture is stirred at room temperature overnight, the chloroform layer is collected therefrom and washed with water, an aqueous sodium bicarbonate solution, diluted hydrochloric acid and water, successively. The chloroform solution is dried and then distilled to remove solvent. The residue thus obtained is purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1)). 8.0 g of methyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate are obtained as colorless oil. Yield: 80.5 %

後処理

  1. temperatureunder ice-cooling
  2. temperatureby heating
  3. distillationfollowed by distillation
  4. customto remove the excess of thionyl chloride)
  5. dissolutionis dissolved in 10 ml of tetrahydrofuran
  6. additionis added dropwise to the suspension
  7. customobtained above
  8. stirringAfter the mixture is stirred at room temperature overnight
  9. customthe chloroform layer is collected
  10. washwashed with water
  11. dry with materialThe chloroform solution is dried
  12. distillationdistilled
  13. customto remove solvent
  14. customThe residue thus obtained
  15. customis purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1))

出典と根拠

ORDレコード
ord-2813aaff273042e3820a4bb2b0273ddf
出典データセット
uspto-grants-1981_03
特許番号
US04256751

関連ノート

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