Trifluoroacetic acid → 2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-mercaptopropionic acid
Reaction equation
[F:1][C:2]([F:41])([C:37]([F:40])([F:39])[F:38])[C@@H:3]([NH:11][C@@H:12]([CH2:16][S:17]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:13]([OH:15])=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.P(CCC(O)=O)(CCC(O)=O)CCC(O)=O.Cl>ClCCl>[F:41][C:2]([F:1])([C:37]([F:38])([F:39])[F:40])[C@@H:3]([NH:11][C@@H:12]([CH2:16][SH:17])[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-tritylsulfanylpropionic acid (6.92 g, 12 mmol) in dichloromethane (10 mL), triethylsilane (3.73 mL, 23.4 mmol) and TFA (3.61 mL, 46.9 mmol) were added at room temperature. The reaction mixture was stirred for 4 h. The solvent and volatiles were evaporated on rotovap, benzene was added to the residue and the mixture was evaporated again to ensure complete removal of excess TFA. The residue was dissolved in 1 N NaOH (50 mL) and extracted with hexanes. To the resulting solution, P(CH2CH2CO2H)3.HCl (0.343 g, 1.2 mmol) was added, and a 0.2 M stock solution of 2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-mercaptopropionic acid was obtained.
Workup
- customThe solvent and volatiles were evaporated on rotovap, benzene
- additionwas added to the residue
- customthe mixture was evaporated again
- customremoval of excess TFA
- dissolutionThe residue was dissolved in 1 N NaOH (50 mL)
- extractionextracted with hexanes
Sources & evidence
- ORD record
- ord-ae613ab7ccc346c48e5efef740fc8c37
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893093B2
Reaction notes
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