Hydrochloric Acid → methyl (3S)-3-acetoxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 1732131Notes

Reaction equation

HRID 1732131 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][N:4]1[C:16]([S:18][CH3:19])=[S:17].[C:20](OC(=O)C)(=[O:22])[CH3:21].Cl>N1C=CC=CC=1>[C:20]([O:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][N:4]1[C:16]([S:18][CH3:19])=[S:17])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 125875Methyl 1,2,3,4-tetrahydro-3-hydroxymethyl-beta-carboline-2-carbodithioate

Product 1

HCID 13631033methyl (3S)-3-acetoxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.88 g of methyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline-2-carbodithioate is dissolved in 10 ml of pyridine. 0.43 ml of acetic anhydride is added to the solution, and the mixture is stirred at room temperature for 13 hours. After the reaction, the mixture is poured into 10% hydrochloric acid and then extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent, whereby 0.95 g of methyl (3S)-3-acetoxymethyl-1,2,3,4-tetrahydro-β-carboline-2-carbodithioate is obtained as white powder. Yield: 95%

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove the solvent

Sources & evidence

ORD record
ord-6a210e75f94f46d2a4d83331d2308095
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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