Trifluoroacetic acid → 2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-mercaptopropionic acid

HRID 1367821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367821
[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

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 2734570Tris(2-carboxyethyl)phosphine hydrochlorideHCID 866248322(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-tritylsulfanylpropionic acid

Produkt 1

HCID 866248312(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-mercaptopropionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe solvent and volatiles were evaporated on rotovap, benzene
  2. additionwas added to the residue
  3. customthe mixture was evaporated again
  4. customremoval of excess TFA
  5. dissolutionThe residue was dissolved in 1 N NaOH (50 mL)
  6. extractionextracted with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ae613ab7ccc346c48e5efef740fc8c37
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893093B2

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