Ethanol → HCID 70217235, compound

HRID 1900988Notes

Reaction equation

HRID 1900988 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[Cl:15][C:16]1[CH:30]=[CH:29][C:19]2[S:20][C:21]([C:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=3)=[CH:22][C:18]=2[CH:17]=1.C(O)C>CS(C)=O>[Cl:15][C:16]1[CH:30]=[CH:29][C:19]2[S:20][C:21]([C:23]3[CH2:24][CH2:25][N:26]([CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]4[CH:14]=[CH:13][CH:12]=[C:11]5[C:7]=4[CH:8]=[CH:9][NH:10]5)[CH2:27][CH:28]=3)=[CH:22][C:18]=2[CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 18797335HCID 18797335, compound

Product 1

HCID 70217235HCID 70217235, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 1 using (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.075 g, 0.042 mmol), and 5-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)benzo[b]thiophene (0.100 g, 0.042 mmol) using ethanol as reaction solvent. Yield 0.103 g (58%) of an orange oil. FDMS m/e=438 (M+ of free base). α[D]589 =+7.3 (c=0.95, dimethylsulfoxide)

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-e5be116a8fc6420b85a981c9cf648fd9
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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