Trifluoroacetic acid → (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol

HRID 1869714Notes

Reaction equation

HRID 1869714 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:5][C@H:6]([NH:20]C(=O)OC(C)(C)C)[C@H:7]([OH:19])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:20][C@@H:6]([CH2:5][C:4]1[CH:28]=[C:29]([F:31])[CH:30]=[C:2]([F:1])[CH:3]=1)[C@H:7]([OH:19])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11441951tert-Butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate

Product 1

HCID 11371095(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate (VII, EXAMPLE 5, 258 mg, 0.59 mmol) is dissolved in methylene chloride (1 mL) at 20-25°, and trifluoroacetic acid (1 mL) is added with stirring under nitrogen. The mixture is stirred at 20-25° for 1 hr, whereupon the mixture is concentrated under reduced pressure to give the title compound. The title compound is used in the next reaction without further purification.

Workup

  1. stirringThe mixture is stirred at 20-25° for 1 hr, whereupon the mixture
  2. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-3711363067f644fb8622cfe3e1289d02
Source dataset
uspto-grants-2009_12
Patent number
US07638646B2

Reaction notes

Loading…