Diazomethane → Methyl (1S,3S)-1-methyl-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249076Notes

Reaction equation

HRID 1249076 reaction equation
[CH3:1][C@H:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][C@@H:4]([C:15]([OH:17])=[O:16])[N:3]1[C:18]([S:20][CH3:21])=[S:19].[N+](=[CH2:24])=[N-]>CCOCC>[CH3:1][C@H:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][C@@H:4]([C:15]([O:17][CH3:24])=[O:16])[N:3]1[C:18]([S:20][CH3:21])=[S:19]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 13561962HCID 13561962, compound

Product 1

HCID 13562002Methyl (1S,3S)-1-methyl-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (1S,3S)-1-methyl-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.28 g), diazomethane [prepared from N-nitrosomethylurea (3.0 g) and 40% NaOH (9 ml)] and ether (100 ml) is allowed to stand under ice-cooling overnight. The resulting precipitates are collected by filtration and dried to give the title compound (1.09 g, 82%), m.p. 229°-230° C.

Workup

  1. temperaturecooling overnight
  2. customThe resulting precipitates
  3. filtrationare collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-602a53f3b9f7439aa305718e20173765
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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