Trifluoroacetic acid → Trifluoroacetic acid

HRID 58790

Reaction equation

HRID 58790 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]([CH2:24][C@H:25]([NH:30][C:31](=[O:43])[C@@H:32]([NH:35]C(OC(C)(C)C)=O)[CH2:33][OH:34])[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>C(Cl)Cl>[NH2:35][C@@H:32]([CH2:33][OH:34])[C:31]([NH: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])=[O:43].[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117690990(S)-methyl 3-(3-(benzyloxy)-4-methoxyphenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanamido)propanoate

Product 2

HCID 6422Trifluoroacetic acidHCID 117690386(S)-methyl 2-((S)-2-amino-3-hydroxypropanamido)-3-(3-(benzyloxy)-4-methoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (20 mL) was added to a solution of (S)-methyl 3-(3-(benzyloxy)-4-methoxyphenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanamido)propanoate (4.4 g, 8.7 mmol) in 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 (S)-methyl 2-((S)-2-amino-3-hydroxypropanamido)-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-774c18d19c134c6a9cb6f6a246ed6bca
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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