(+)-Styrene oxide → HCID 54086303, compound

HRID 1381264Notes

Reaction equation

HRID 1381264 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>[OH:21][C@H:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:20][N:1]([CH2:20][C@H:19]([OH:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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

5

Reactant 2

HCID 114705(+)-Styrene oxideHCID 198091145-(3-Aminopropyl)thiophene-2-carboxamide

Product 1

HCID 54086303HCID 54086303, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

30 g of 5-(3-aminopropyl)-2-thiophenecarboxamide and 20.2 ml of (R)-phenylethylene oxide were stirred at 95° for 24 hours in 400 ml of dimethyl sulphoxide. After cooling, the mixture was diluted with 1.3 l of water and extracted three times with about 600 ml of methylene chloride. The methylene chloride solutions were washed twice with water, dried over sodium sulphate and evaporated in vacuo. Chromatography of the residue on silica gel with ether/methanol gave 21 g of 5-[3-[bis[(R)-β-hydroxyphenethyl]amino]propyl]-2-thiophenecarboxamide; UV: ε276 =9900; [α]D =-69° (c=0.1% in dioxan).

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with about 600 ml of methylene chloride
  3. washThe methylene chloride solutions were washed twice with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6250959586334cffa05c275bd9458dc3
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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