Hydrochloric Acid → HCID 13711346, compound

HRID 1732127Notes

Reaction equation

HRID 1732127 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][NH:8][C@H:7]([C:15]([OH:17])=[O:16])[CH2:6][C:5]2=1.[C:18](=[S:20])=[S:19].[CH3:21]I.Cl>CS(C)=O.O.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][N:8]([C:18]([S:20][CH3:21])=[S:19])[C@H:7]([C:15]([OH:17])=[O:16])[CH2:6][C:5]2=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 13037302HCID 13037302, compound

Product 1

HCID 13711346HCID 13711346, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

65 mg of (3S)-6-fluoro-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid are dissolved in a mixture of one ml of dimethylsulfoxide and 0.5 ml of water. 0.02 ml of carbon disulfide and 0.093 ml of triethylamine are added to the mixture, and the mixture is stirred at room temperature for 20 minutes. 0.021 ml of methyl iodide is added to the mixture, and the mixture is stirred at room temperature for 16 hours. Water is added to the mixture, and the aqueous solution is acidified with 10% HCl and extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. The residue is purified by silica gel thin layer chromatography (Solvent; chloroform:methanol:acetic acid=93:6:1). 37 mg of (3S)-6-fluoro-2-(methylthio)thiocarbonyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid are obtained as pale yellow powder.

Workup

  1. stirringthe mixture is stirred at room temperature for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica gel thin layer chromatography (Solvent; chloroform:methanol:acetic acid=93:6:1)

Sources & evidence

ORD record
ord-02f6d84b06b14d5fbbf939d0b0d5c123
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

Loading…