1,2-Dichloroethane → (2S)-3,3,4,4,4-pentafluorobutan-2-yl 2-(6-methoxynaphthalen-2-yl)propanoate

HRID 1181643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181643
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[CH:4]=1.[F:18][C:19]([F:27])([C:23]([F:26])([F:25])[F:24])[CH:20](O)[CH3:21].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][O:13][C:10]1[CH:9]=[C:6]2[C:5](=[CH:12][CH:11]=1)[CH:4]=[C:3]([CH:2]([CH3:1])[C:15]([O:17][C@H:20]([C:19]([F:27])([F:18])[C:23]([F:26])([F:25])[F:24])[CH3:21])=[O:16])[CH:8]=[CH:7]2

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 789913,3,4,4,4-Pentafluorobutan-2-olHCID 156391Naproxen

Produkt 1

HCID 87271567(2S)-3,3,4,4,4-pentafluorobutan-2-yl 2-(6-methoxynaphthalen-2-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of (S)-naproxen (9.23 g, 40.1 mmol), racemic 3,3,4,4,4-pentafluoro-2-butanol (6.58 g, 40.1 mmol), EDC (9.20 g, 48.0 mmol) and DMAP (4.89 g, 40.0 mmol) was dissolved in CH2Cl2 (40 mL) at room temperature. After stirring for 8 h at room temperature, the mixture was diluted with CH2Cl2, then washed successively with 1 N HCl, sat. NaHCO3, and brine. After drying over Na2SO4 and concentrating, a mixture of diastereomeric naproxen esters was obtained as a white solid.

Aufarbeitung

  1. washwashed successively with 1 N HCl, sat. NaHCO3, and brine
  2. dry with materialAfter drying over Na2SO4
  3. concentrationconcentrating
  4. additiona mixture of diastereomeric naproxen esters
  5. customwas obtained as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-f9477dbbfb9148e6ae9d8d7fe68598de
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285671B2

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