Water → (3S)-2-[(Benzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1249038Notes

Reaction equation

HRID 1249038 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.C([O-])([O-])=O.[K+].[K+].O.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:32](=[S:34])=[S:33]>C(O)C>[CH2:24]([S:34][C:32]([N:2]1[C@H: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:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6348Carbon DisulfideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 449440(3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 13561932(3S)-2-[(Benzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as described in Example 16, (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (21.6 g), K2CO3 (13.8 g), water (550 ml), ethanol (550 ml), carbon disulfide (6 ml) and benzyl bromide (14 ml) are reacted and treated. The residue is purified by silica gel column chromatography (solvent, chloroform:methanol=10:1) to give the title compound (20 g, 52.3%) as powder.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e2dfa1bbd8234cb797eda786eac67703
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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