Trifluoroacetic acid → Trifluoroacetic acid

HRID 58798Notes

Reaction equation

HRID 58798 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC([NH:15][C@@H:16]([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=O)(C)(C)C>C(Cl)Cl>[NH2:15][C@@H:16]([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681449Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-methoxypyridin-4-yl)propanoate

Product 2

HCID 6422Trifluoroacetic acidHCID 117608201(S)-methyl 2-amino-3-(2-methoxypyridin-4-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5 mL) was added to a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(2-methoxypyridin-4-yl)propanoate (2.4 g, 7.7 mmol) in CH2Cl2 (10 mL) at 0° C. with stirring. The mixture was stirred for 1 h and then concentrated to dryness. The residue was azeotroped three times with EtOAc (10 mL for each portion) to remove residual TFA to afford crude (S)-methyl 2-amino-3-(2-methoxypyridin-4-yl)propanoate as its TFA salt.

Workup

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

Sources & evidence

ORD record
ord-bf12afae3461471e9db3f5d4a111db16
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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