Carbon Disulfide → 4-(N-Formylamino)benzyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65069Notes

Reaction equation

HRID 65069 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][NH:4]1.C(N(CC)CC)C.[C:23](=[S:25])=[S:24].[CH:26]([NH:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1)=[O:27]>CN(C)C=O.CS(C)=O>[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:23]([S:25][CH2:33][C:32]1[CH:35]=[CH:36][C:29]([NH:28][CH:26]=[O:27])=[CH:30][CH:31]=1)=[S:24]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carbolineHCID 202257044-(N-formylamino)benzyl chloride

Product 1

HCID 133929854-(N-Formylamino)benzyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 58%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

In the same manner as described in Example 29 by using (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.21 g), triethylamine (0.84 ml), CS2 (0.36 ml), 4-(N-formylamino)benzyl chloride (1.02 g) and dimethylsulfoxide (30 ml), there is prepared the title compound (1.43 g, 58%) as pale yellow powder, [α]D20 +120.2° (c=1.0, dimethylformamide); NMR (DMSO-d6, δ): 4.54 (s, 2H, ##STR12## Mass m/e: 244 (M+ -- ##STR13##

Sources & evidence

ORD record
ord-e17f56a49aa349adbb9e58a2e2bdf171
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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