Methanol → Methyl (3S)-2-[(4-chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249067Notes

Reaction equation

HRID 1249067 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][S:7][C:8]([N:10]2[C@H:22]([C:23]([OH:25])=[O:24])[CH2:21][C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:12]=3[CH2:11]2)=[S:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:32]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][S:7][C:8]([N:10]2[C@H:22]([C:23]([O:25][CH3:32])=[O:24])[CH2:21][C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:12]=3[CH2:11]2)=[S:9])=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 13561935(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Product 1

HCID 13561998Methyl (3S)-2-[(4-chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 50%

Procedure

(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2.08 g) is dissolved in methanol (30 ml) and thereto is added dropwise thionyl chloride (0.94 ml) at -20° C. The mixture is stirred at 50°-60° C. for 5 hours and then distilled to remove the solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried, treated with active carbon and distilled to remove the solvent. The residue is recrystallized from ethyl acetate-n-hexane to give the title compound (1.08 g, 50%) as colorless needles, mp 181°-182° C. (decomp.).

Workup

  1. distillationdistilled
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed with water
  5. customdried
  6. additiontreated with active carbon
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b938b2a1cc6c4befb1dec8ad01b397c6
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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