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

HRID 260323Notes

Reaction equation

HRID 260323 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-8440c605c468446ca404bbc575434c28
Source dataset
uspto-grants-1996_06
Patent number
US05527795

Reaction notes

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