Water → HCID 54086302, compound

HRID 1381262Notes

Reaction equation

HRID 1381262 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.[OH2:22]>CS(C)=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:22])[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 3

HCID 962WaterHCID 114946(S)-styrene oxideHCID 198091145-(3-Aminopropyl)thiophene-2-carboxamide

Product 1

HCID 54086302HCID 54086302, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5 g of 5-(3-aminopropyl)-2-thiophenecarboxamide and 3.4 ml of (S)-phenylethylene oxide were stirred at 95° for 26 hours in 68 ml of dimethyl sulphoxide. The mixture was poured into 200 ml of water and extracted three times with 150 ml of methylene chloride. The methylene chloride solutions were washed with water, dried and evaporated in vacuo. Chromatography of the residue on silica gel with ether/methanol gave 2.85 g of 5-[3-[bis-[(S)-β-hydroxyphenethyl]amino]propyl]-2-thiophenecarboxamide; [α]D =+76° (c=0.1% in dioxan); UV: ε277 =10390.

Workup

  1. extractionextracted three times with 150 ml of methylene chloride
  2. washThe methylene chloride solutions were washed with water
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-647f1313ff1f498dbf4817691d4ff232
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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