Ethanol → HCID 58120259, Verbindung

HRID 533384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533384
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:19])[CH2:14][O:15][CH:16]([CH3:18])[CH3:17])[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1F.CCO>CN(C=O)C.Cl>[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[O:19][C@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:14][O:15][CH:16]([CH3:17])[CH3:18]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 123112Benzene, 2,4-dichloro-1-fluoro-HCID 66859524(S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Produkt 1

HCID 58120259HCID 58120259, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (25.0 mg, 91.4 μmol) was dissolved in DMF (190 μL). NaH (2.6 mg, 109.7 μmol) was added and the mixture was stirred at room temperature for 15 minutes. 2,4-Dichloro-1-fluorobenzene (21.4 μL, 182.9 mmol) was added and the mixture was stirred at 70° C. for 3 hours. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (949 μL, 1.1 mmol) and stirred overnight. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt oil (29.5 mg, 97% purity). MS m/z: [M+H]+ calcd for C15H21Cl2NO2, 318.10. found 318.0.

Aufarbeitung

  1. stirringthe mixture was stirred at 70° C. for 3 hours
  2. concentrationThe mixture was concentrated
  3. stirringstirred overnight
  4. concentrationThe product was concentrated
  5. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-86ceadc0774d401895f83a1946e4f510
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853255B2

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