Methyl iodide → (3RS)-2-[(Methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1249026Notes

Reaction equation

HRID 1249026 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][C@@H:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].[C:19](=[S:21])=[S:20].[CH3:22]I>C(O)C>[CH3:22][S:20][C:19]([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:21]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 449440(3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 13561913(3RS)-2-[(Methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as described in Example 2, (i), (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (42.25 g), KOH (23.38 g), carbon disulfide (12.1 ml), methyl iodide (16.3 ml) and 50% ethanol (600 ml) are reacted. The product is crystallized from chloroform to give the title compound (50.2 g, 59%), m.p. 111°-113° C., NMR (CDCl3, δ): 2.68 (s, 3H, N--CSSCH3), Mass (m/e): 306 (M+), 258 (M+ --CH3SH).

Workup

  1. customare reacted
  2. customThe product is crystallized from chloroform

Sources & evidence

ORD record
ord-740c0a75703a4de5ba2d62ca43d270b2
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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