Trifluoroacetic acid → (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoic acid hydrochloride

HRID 1160404Notes

Reaction equation

HRID 1160404 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])[CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])[CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 595162251,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoate

Product 1

HCID 68484641(3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoate (0.33 g, 0.94 mmol) in CH2Cl2 (2 mL) was treated with TFA (1 mL) for 1.5 h and the reaction was evaporated thoroughly. The residue was treated with 4N HCl in dioxane (4 mL) and then concentrated (this step was done twice) and the crude product was used directly in the next step.

Workup

  1. customthe reaction was evaporated thoroughly
  2. additionThe residue was treated with 4N HCl in dioxane (4 mL)
  3. concentrationconcentrated (this step

Sources & evidence

ORD record
ord-3a71f1f5eb4d434a888f348f917d3235
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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