2,2,3,3,3-Pentafluoropropanol → 2(R)-(2,2,3,3,3-pentafluoropropylamino)-3-tritylsulfanylpropionic acid

HRID 907654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907654
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3]O.CCN(C(C)C)C(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[C:34]([S:53][CH2:54][C@@H:55]([C:57]([OH:59])=[O:58])[NH2:56])([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][NH:56][C@@H:55]([CH2:54][S:53][C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:57]([OH:59])=[O:58]

Komponenten

6

Edukt 4

HCID 98722,2,3,3,3-PentafluoropropanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 76044S-Trityl-L-CysteineHCID 81531Diisopropylethylamine

Produkt 1

HCID 866100972(R)-(2,2,3,3,3-pentafluoropropylamino)-3-tritylsulfanylpropionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a −78° C. methylene chloride solution (75 mL) of 2,2,3,3,3-pentafluoropropan-1-ol (1.5 g, 10.0 mmol) and DIPEA (6.1 mL, 35.0 mmol) was added triflic anhydride (1.78 mL, 10.5 mmol). After 2.5 h, S-tritylcysteine was added all at once and the reaction mixture was stirred at 0° C. for 80 min. The reaction mixture was stirred at RT for 18 h and then concentrated on the rotovap. Ethyl acetate was added and the reaction mixture was washed with 1N HCl. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (3 hexanes/1 ethyl acetate+1% acetic acid) to provide 2(R)-(2,2,3,3,3-pentafluoropropylamino)-3-tritylsulfanylpropionic acid (3.29 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT for 18 h
  2. concentrationconcentrated on the rotovap
  3. additionEthyl acetate was added
  4. washthe reaction mixture was washed with 1N HCl
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (3 hexanes/1 ethyl acetate+1% acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-add0f3db8c3045ca9b395a3f3ac8cae2
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013183B2

Notizen zur Reaktion

Wird geladen…