Ethanol → (3R)-2-[(Benzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1249037

反応式

HRID 1249037 の反応式
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@H:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[Na+].C(O)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:30](=[S:32])=[S:31]>>[CH2:22]([S:32][C:30]([N:2]1[C@@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 675102D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

生成物 1

HCID 13561931(3R)-2-[(Benzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

実験手順

To a mixture of (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (5.4 g), 2N NaOH (25 ml) and 50% ethanol (70 ml) is added dropwise carbon disulfide (1.5 ml) at room temperature. The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise benzyl bromide (3.5 ml), and the mixture is further stirred at the same temperature for 3 hours and then distilled to remover the solvent. To the residue is added water, and the mixture is extracted with ether. The aqueous layer is acidified with 10% HCl, extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:methanol=20:1) to give the title compound (4.5 g) as pale yellow powder.

後処理

  1. stirringthe mixture is further stirred at the same temperature for 3 hours
  2. distillationdistilled
  3. additionTo the residue is added water
  4. extractionthe mixture is extracted with ether
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-0271a25bd06d4969a382bfb50786e4d6
出典データセット
uspto-grants-1986_12
特許番号
US04628057

関連ノート

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