Trifluoroacetic acid → Trifluoroacetic acid

HRID 58788Notes

Reaction equation

HRID 58788 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH2:24][C@H:25]([NH:30]C(OC(C)(C)C)=O)[C:26]([O:28][CH3:29])=[O:27])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[NH2:30][C@@H:25]([CH2:24][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:17]=1)[C:26]([O:28][CH3:29])=[O:27].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117690479(S)-methyl 3-(3-(benzyloxy)-4-methoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Product 2

HCID 6422Trifluoroacetic acidHCID 117690774(S)-methyl 2-amino-3-(3-(benzyloxy)-4-methoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (TFA; 25 mL) was added to a solution of (S)-methyl 3-(3-(benzyloxy)-4-methoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate (5.00 g, 12.0 mmol) in dichloromethane (CH2Cl2; 50 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 (20 mL for each portion) to remove residual TFA to afford crude compound (S)-methyl 2-amino-3-(3-(benzyloxy)-4-methoxyphenyl)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 (20 mL for each portion)
  4. customto remove residual TFA

Sources & evidence

ORD record
ord-36290195f54340609b22129873cef33a
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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