Trifluoroacetic acid → Methyl 2-(aminomethyl)pent-4-enoate

HRID 2396016Notes

Reaction equation

HRID 2396016 reaction equation
C(OC([NH:8][CH2:9][CH:10]([CH2:15][CH:16]=[CH2:17])[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:15]([CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:9][NH2:8])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 10728929Methyl 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pentenoate

Product 1

HCID 22401195Methyl 2-(aminomethyl)pent-4-enoateYield 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve N-(t-butyloxycarbonyl)-2-(2-propenyl)-β-alanine, methyl ester(5.6 g, 23.0 mmol) in methylene chloride (25 mL) and treat with trifluoroacetic acid (15 mL). Stir for three hours and remove the volatiles in vacuo. Treat the residue with water, make basic with sodium hydroxide (1.0 g, 25 mmol) and extract with ethyl acetate. Separate the organic phase and dry (Na2SO4). Evaporate to give 4.0 g of the title compound as an oil in ethyl acetate.

Workup

  1. customremove the volatiles in vacuo
  2. additionTreat the residue with water
  3. extractionextract with ethyl acetate
  4. customSeparate the organic phase
  5. dry with materialdry (Na2SO4)
  6. customEvaporate

Sources & evidence

ORD record
ord-62df512d0c2b48a7a5207029a62f8383
Source dataset
uspto-grants-1996_02
Patent number
US05491143

Reaction notes

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