Trifluoroacetic acid → 2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-mercaptopropionic acid
反応式
[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]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
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.
後処理
- 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
出典と根拠
- ORDレコード
- ord-ae613ab7ccc346c48e5efef740fc8c37
- 出典データセット
- uspto-grants-2011_02
- 特許番号
- US07893093B2
反応ノート
読み込み中…