Hydrochloric Acid → (3R)-3-acetoxy-1-(tert-butoxycarbonyl)-L-proline

HRID 1424208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424208
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].[C:14]([N:21]1[CH2:28][CH2:27][C@@H:26]([OH:29])[C@H:22]1[C:23]([OH:25])=[O:24])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl>O>[C:7]([O:29][C@@H:26]1[CH2:27][CH2:28][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:22]1[C:23]([OH:25])=[O:24])(=[O:9])[CH3:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11096439(2S,3R)-3-Hydroxypyrrolidine-2-carboxylic acid, N-BOC protected

Produkt 1

HCID 86699073(3R)-3-acetoxy-1-(tert-butoxycarbonyl)-L-prolineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Pyridine (5 mL) and acetic anhydride (2 mL) were added to N-boc-cis-3-hydroxy-L-proline (400 mg, 1.73 mmol) and the reaction was stirred for 4 hours at room temperature. The reaction was diluted with water, acidified with 1N HCl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the title compound (370 mg, 78%).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0c43d5cde72245ed8f85af6c515c04db
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927587B2

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