Hydrochloric Acid → (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid

HRID 858928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858928
C[O:2][C:3]([C@H:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[O:4].Cl>O1CCOCC1>[F:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([N:7]2[C:8](=[O:10])[CH2:9][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6]2)=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68614551(S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Produkt 1

HCID 67409315(S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 74.6 mmol of (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester in 650 ml of dioxane was treated with 175 ml of hydrochloric acid (37%). The mixture was heated at 50° C. for 18 h in a closed flask. The solution was evaporated under reduced pressure to yield the crude acid as a yellow solid. The crude acid was triturated at 0° C. in 50 ml of ethyl acetate. The solid was collected on a filter funnel and then dried under high vacuum to yield (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid as a yellowish solid; MS: m/e=330 (M+H)+.

Aufarbeitung

  1. customThe solution was evaporated under reduced pressure
  2. customto yield the crude acid as a yellow solid
  3. customThe crude acid was triturated at 0° C. in 50 ml of ethyl acetate
  4. customThe solid was collected on a filter funnel
  5. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-45bd6c3c177e46c180abb653b7ab872b
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148362B2

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