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

HRID 1249041Notes

Reaction equation

HRID 1249041 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.[OH-].[Na+].C(O)C.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.[C:31](=[S:33])=[S:32]>>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][S:33][C:31]([N:2]2[C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:32])=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 449440(3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 13561935(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidYield 69%

Procedure

In the same manner as described in Example 16, (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.08 g), 2N NaOH (5 ml), 50% ethanol (15 ml), carbon disulfide (0.3 ml) and 4-chlorobenzyl chloride (1.13 g) are reacted and treated. The product is crystallized from n-hexane to give the title compound (1.44 g, 69%), m.p. 139°-141° C. (decomp.).

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is crystallized from n-hexane

Sources & evidence

ORD record
ord-74bd839771bb42f5ab76ee0c3ba81abe
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

Loading…