1-Phenethylamine, (-)- → HCID 54152570, compound

HRID 232514Notes

Reaction equation

HRID 232514 reaction equation
[C:1]([C:5]1[O:9][C:8]([C:10]([O:12]CC)=O)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]1([C@@H:21]([NH2:23])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:15]1([C@@H:21]([NH:23][C:10]([C:8]2[O:9][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[N:6][N:7]=2)=[O:12])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 23358677HCID 23358677, compound

Product 1

HCID 54152570HCID 54152570, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-tert-butyl-[1,3,4]oxadiazole-2-carboxylate (1.38 g, 7 mmol) and (S)-1-phenylethylamine (1.70 g, 14 mmol) in absolute ethanol (25 ml) is refluxed for 6 hours. The solvent is evaporated in vacuo and the residue is purified by flash column chromatography (silica gel, hexane/ethyl acetate 4:1 v/v) to give (S)-5-tert-butyl-[1,3,4]oxadiazole-2-carboxylic acid (1-phenylethyl)amide (1.76 g, 92%) as colourless crystals, m.p. 123°-125° C.

Workup

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is purified by flash column chromatography (silica gel, hexane/ethyl acetate 4:1 v/v)

Sources & evidence

ORD record
ord-03d6f2cfd98a4348bd21e771829582fa
Source dataset
uspto-grants-1997_01
Patent number
US05591695

Reaction notes

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