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

HRID 1249034Notes

Reaction equation

HRID 1249034 reaction equation
[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][CH:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].C(O)C.[CH3:22][S:23][CH2:24]Cl.[C:26](=[S:28])=[S:27]>>[CH3:22][S:23][CH2:24][S:28][C:26]([N:2]1[CH: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:27]

Participants

6

Reactant 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 16916Chloromethyl methyl sulfideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 54525122(3RS)-2-[(Methylthiomethylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Procedure

In the same manner as described in Example 6, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (3.24 g), KOH (1.75 g), 50% ethanol (70 ml), carbon disulfide (0.91 ml) and methylthiomethyl chloride (1.74 g) are reacted and treated. The product thus obtained is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1) to give the title compound (2.61 g) as a pale yellow powder.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product thus obtained
  4. customis purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1)

Sources & evidence

ORD record
ord-5c60ff2ae14e415c93131123ce84b81c
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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