(S)-styrene oxide → HCID 53677256, compound

HRID 1381261Notes

Reaction equation

HRID 1381261 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]([NH2:12])=[O:11])=[CH:7][CH:6]=1.[C:13]1([C@@H:19]2[O:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O.O.C(Cl)Cl>[OH:21][C@@H:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:20][NH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]([NH2:12])=[O:11])=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 114946(S)-styrene oxideHCID 198091145-(3-Aminopropyl)thiophene-2-carboxamide

Product 1

HCID 53677256HCID 53677256, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-(3-Aminopropyl)-2-thiophenecarboxamide was heated with (S)-phenylethylene oxide at b 95° in dimethyl sulphoxide. The mixture was diluted with water and methylene chloride and the aqueous phase was extracted twice with methylene chloride. The methylene chloride phases were washed with water, dried over sodium sulphate and evaporated in vacuo. Chromatography of the residue with methanol on silica gel gave 5-[3-[[(S)-β-hydroxyphenethyl]amino]propyl]-2-thiophenecarboxamide of melting point 94°-96°; [α]589 =+19° (c=0.1% in dioxan); ε256 =8490; ε275 =10780.

Workup

  1. extractionthe aqueous phase was extracted twice with methylene chloride
  2. washThe methylene chloride phases were washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-449ca5903379446780bc0a36ac010c9a
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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