Bromomethylcyclopropane → Nalpha-Cyclopropylmethyl-L-phenylalanine Amide

HRID 894276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894276
Cl.[NH2:2][C@H:3]([C:11]([NH2:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+].Br[CH2:20][CH:21]1[CH2:23][CH2:22]1>C(O)C>[CH:21]1([CH2:20][NH:2][C@H:3]([C:11]([NH2:13])=[O:12])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 11953719Phenylalanine amide hydrochloride

Produkt 1

HCID 54321039Nalpha-Cyclopropylmethyl-L-phenylalanine AmideAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 100 ml. of anhydrous ethyl alcohol were added 8 grams (0.04 mole) of L-phenylalanine amide hydrochloride. To the mixture then were added 13.4 grams (0.16 mole) of solid anhydrous sodium bicarbonate and 6.44 grams (0.048 mole) of bromomethylcyclopropane. The mixture was refluxed for seven hours and then was evaporated in vacuo to an oil. The oil was dissolved in ethyl acetate, and the ethyl acetate solution was extracted with water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to an oil. The oil was applied to a 3×50 cm. column of Grace and Davison grade 62 silica gel in chloroform. The product was eluted with a gradient of chloroform containing up to 5 percent methanol. The product was isolated according to the thin-layer profile of the fractions collected to give 3.41 grams (39 percent) of the title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for seven hours
  2. customwas evaporated in vacuo to an oil
  3. dissolutionThe oil was dissolved in ethyl acetate
  4. extractionthe ethyl acetate solution was extracted with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated in vacuo to an oil
  7. washThe product was eluted with a gradient of chloroform containing up to 5 percent methanol
  8. customThe product was isolated
  9. customcollected

Quellen und Nachweise

ORD-Eintrag
ord-07f1715041954ce48d663284fa0f16b6
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04283330

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