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

HRID 1249040

Reaktionsgleichung

Reaktionsgleichung von HRID 1249040
[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.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.[C:31](=[S:33])=[S:32]>>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][S:33][C:31]([N:2]2[C@@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:32])=[CH:25][CH:24]=1

Komponenten

6

Edukt 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 675102D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

Produkt 1

HCID 13561934(3R)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidAusbeute 57 %

Versuchsvorschrift

In the same manner as described in Example 16, (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (5.4 g), 2N NaOH (25 ml), 50% ethanol (70 ml), carbon disulfide (1.45 ml) and 4-chlorobenzyl chloride (5.65 g) are reacted and treated. The residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1) to give the title compound (5.86 g, 57%) as pale yellow powder.

Aufarbeitung

  1. customare reacted
  2. additiontreated
  3. customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7d7cac32ca4a4125a625bea79f8322ce
Quelldatensatz
uspto-grants-1986_12
Patentnummer
US04628057

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