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Lithium Hydroxide → (S)-3-cyclohexyl-2-[2-oxo-4-(3-trifluoromethoxy-phenoxy)-2,5-dihydro-pyrrol-1-yl]-propionic acid

HRID 19287
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 19287
C[O:2][C:3](=[O:30])[C@@H:4]([N:12]1[CH2:16][C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=2)=[CH:14][C:13]1=[O:29])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1.O>[CH:6]1([CH2:5][C@H:4]([N:12]2[CH2:16][C:15]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:26])([F:27])[F:28])[CH:19]=3)=[CH:14][C:13]2=[O:29])[C:3]([OH:30])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 66894937(S)-3-cyclohexyl-2-[2-oxo-4-(3-trifluoromethoxy-phenoxy)-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

Produkt 1

HCID 66895246(S)-3-cyclohexyl-2-[2-oxo-4-(3-trifluoromethoxy-phenoxy)-2,5-dihydro-pyrrol-1-yl]-propionic acidAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a stirred solution of (S)-3-cyclohexyl-2-[2-oxo-4-(3-trifluoromethoxy-phenoxy)-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (0.520 g, 0.001 mol) in tetrahydrofuran-water (3:1, 20 mL) was added lithium hydroxide (153 mg, 0.006 mol). The reaction mixture was stirred at 23° C. for 2 h. After this time, the mixture was concentrated and the reaction mixture was diluted with water. The reaction mixture was acidified with 2N hydrochloric acid, during which time precipitation occurred. The precipitate was removed by filtration, washed with cold water and dried in vacuo to obtain (S)-3-cyclohexyl-2-[2-oxo-4-(3-trifluoromethoxy-phenoxy)-2,5-dihydro-pyrrol-1-yl]-propionic acid (380 mg, 76%) as a light yellow solid.

Aufarbeitung

  1. concentrationAfter this time, the mixture was concentrated
  2. additionthe reaction mixture was diluted with water
  3. customThe reaction mixture was acidified with 2N hydrochloric acid, during which time precipitation
  4. customThe precipitate was removed by filtration
  5. washwashed with cold water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ba2b91ea467744d1b64206bf3291f8df
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741327B2

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