Hydrochloric Acid → HCID 58392516, Verbindung

HRID 561517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561517
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[N:18](C(OC(C)(C)C)=O)[CH:17]=2)[CH:9]([CH3:15])[C:10](OCC)=[O:11])=[C:4]([F:35])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:9]([CH3:15])[CH2:10][OH:11])=[C:4]([F:35])[CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392467HCID 58392467, Verbindung

Produkt 1

HCID 58392516HCID 58392516, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 200 mg of the compound from Example 36A with a purity of 90% (0.35 mmol) in 4 ml of tetrahydrofuran was added dropwise to 1.2 ml (1.2 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 2 ml of tetrahydrofuran at RT under argon. The mixture was stirred at RT for 15 min and then 1N hydrochloric acid was added. The mixture was extracted with dichloromethane, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 66 mg (51% of theory) of the title compound as mixture of diastereomers.

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-415ff0bf62244d4597ae2b82417b2ad7
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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