Trifluoroacetic acid → 3-((2R)-2-(methylamino)-3-phenylpropionylamino)propyl acetate

HRID 1268594Notes

Reaction equation

HRID 1268594 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:27])[C@H:10]([N:18](C(OC(C)(C)C)=O)[CH3:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:27])[C@H:10]([NH:18][CH3:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 539060843-((2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-phenylpropionylamino)propyl acetate

Product 1

HCID 540549383-((2R)-2-(methylamino)-3-phenylpropionylamino)propyl acetateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-((2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-phenylpropionylamino)propyl acetate (862 mg, 2.28 mmol) in dichloromethane (3 mL) was cooled to 0° C. Trifluoroacetic acid (3 mL) was added. The solution was stirred for 10 min. The solvents were removed in vacuo without warming. The residue was dissolved in dichloromethane (50 mL) and the solvent was removed in vacuo. The procedure was repeated twice. The crude product was purified by flash chromatography on silica (70 g) with dichloromethane/methanol/25% ammonia in water (100:10:1) to give 602 mg of 3-((2R)-2-(methylamino)-3-phenylpropionylamino)propyl acetate.

Workup

  1. customThe solvents were removed in vacuo
  2. temperaturewithout warming
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (70 g) with dichloromethane/methanol/25% ammonia in water (100:10:1)

Sources & evidence

ORD record
ord-8478c45fd80649298aa8afcd4f340fc9
Source dataset
uspto-grants-2003_04
Patent number
US06555570B2

Reaction notes

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