Methanol → [(S)-1-((3S,4S,7R)-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

HRID 229829

Reaktionsgleichung

Reaktionsgleichung von HRID 229829
C(OC([N:11]1[CH2:17][C@H:16]([OH:18])[C@@H:15]([NH:19][C:20](=[O:34])[C@@H:21]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:14][CH2:13][C@H:12]1[CH3:35])=O)C1C=CC=CC=1.CO.[H][H]>CCOC(C)=O.[Pd]>[C:30]([O:29][C:27](=[O:28])[NH:26][C@H:21]([C:20](=[O:34])[NH:19][C@H:15]1[CH2:14][CH2:13][C@@H:12]([CH3:35])[NH:11][CH2:17][C@@H:16]1[OH:18])[CH2:22][CH:23]([CH3:25])[CH3:24])([CH3:32])([CH3:33])[CH3:31]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 69000072(2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 58665057[(S)-1-((3S,4S,7R)-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.169 g, 0.344 mmol) was dissovled in EtOAc (3 ml), MeOH (1 ml). Then 10% Pd/C (0.183 g, 0.172 mmol) was added and the reaction was stirred overnight under a balloon filled with hydrogen gas. The reaction mixture was filtered through Celite, concentrated in vacuo by rotary evaporation and was used in the next reaction without further purification (0.126 g): Electrospray mass spec: M+H+=358.11.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo by rotary evaporation
  3. customwas used in the next reaction without further purification (0.126 g)

Quellen und Nachweise

ORD-Eintrag
ord-0b177a3d69704038ba438c51f9ca16b0
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563784B2

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