Bromomethylcyclopropane → Nalpha-Cyclopropylmethyl-L-phenylalanine Amide

HRID 894276Notes

Reaction equation

HRID 894276 reaction equation
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

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 11953719Phenylalanine amide hydrochloride

Product 1

HCID 54321039Nalpha-Cyclopropylmethyl-L-phenylalanine AmideYield 39.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07f1715041954ce48d663284fa0f16b6
Source dataset
uspto-grants-1981_08
Patent number
US04283330

Reaction notes

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