Trifluoroacetic acid → d-Valine benzyl ester trifluoroacetic acid salt

HRID 2297966Notes

Reaction equation

HRID 2297966 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[C@@H:10]([CH:19]([CH3:21])[CH3:20])[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>C(Cl)Cl>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[CH2:1]([O:8][C:9](=[O:22])[C@@H:10]([CH:19]([CH3:20])[CH3:21])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11243734(R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

Product 1

HCID 69764497d-Valine benzyl ester trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

N-Tert-butoxycarbonyl-D-valine benzyl ester (70.7 g, 0.23 mol) was dissolved in a mixture of trifluoroacetic acid and methylene chloride (150 mL in 1:4 ratio) and the reaction mixture was heated at 50-60° C. After 6 h, the reaction mixture was concentrated to give D-valine benzyl ester trifluoroacetic acid salt (156.8 g) as a viscous oil which was converted to the free amine just prior to use.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ada56c6a23904ef2a227aa1ac2747bed
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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