Trifluoroacetic acid → (2R)-2-(2-aminoethylamino)-3-phenylpropionic acid methyl ester

HRID 581193Notes

Reaction equation

HRID 581193 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:12][CH2:13][CH2:14][NH:15]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:12][CH2:13][CH2:14][NH2:15])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54571530(2R)-2-(2-(tert-butoxycarbonylamino)ethylamino)-3-phenylpropionic acid methyl ester

Product 1

HCID 54002275(2R)-2-(2-aminoethylamino)-3-phenylpropionic acid methyl esterYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-(2-(tert-Butoxycarbonylamino)ethylamino)-3-phenylpropionic acid methyl ester (1.32 g; 4.094 mmol) was dissolved in methylene chloride (10 ml) and trifluoroacetic acid (10 ml) was added. The reaction mixture was stirred for 1 hour at room temperature. The solvent was evaporated in vacuo and the residue was dissolved in methylene chloride (5 ml) and evaporated in vacuo. Methylene chloride (5 ml) was added and evaporated in vacuo to afford 1.14 g of (2R)-2-(2-aminoethylamino)-3-phenylpropionic acid methyl ester as a trifluoroacetate salt.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride (5 ml)
  3. customevaporated in vacuo
  4. additionMethylene chloride (5 ml) was added
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c18f76108796453d819671c1d1ec5c78
Source dataset
uspto-grants-1999_07
Patent number
US05919777

Reaction notes

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