Trifluoroacetic acid → Trifluoroacetic acid

HRID 58856Notes

Reaction equation

HRID 58856 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH2:23][C@H:24]([NH:29]C(OC(C)(C)C)=O)[C:25]([O:27][CH3:28])=[O:26])[CH:19]=[CH:20][C:21]=1[CH3:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:29][C@@H:24]([CH2:23][C:18]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:17]=1)[C:25]([O:27][CH3:28])=[O:26].[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117690422(S)-methyl 3-(3-(benzyloxy)-4-methylphenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Product 2

HCID 6422Trifluoroacetic acidHCID 117690752(S)-methyl 2-amino-3-(3-(benzyloxy)-4-methylphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To TFA (5 mL) was added to a solution of (S)-methyl 3-(3-(benzyloxy)-4-methylphenyl)-2-((tert-butoxycarbonyl)amino)propanoate (1.0 g, 2.5 mmol) in DCM (10 mL) at 0° C. with stirring. The mixture was stirred for 1 h and then concentrated to dryness. The residue was azeotroped with EtOAc (10 mL×3) to remove residual TFA and afford crude (S)-methyl 2-amino-3-(3-(benzyloxy)-4-methylphenyl)propanoate as its TFA salt.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. concentrationconcentrated to dryness
  3. customThe residue was azeotroped with EtOAc (10 mL×3)
  4. customto remove residual TFA

Sources & evidence

ORD record
ord-aaa47e7ff1884e99861885766d410272
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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