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

HRID 1790623

Reaktionsgleichung

Reaktionsgleichung von HRID 1790623
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 dissolved 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-65dfd71e9fca499fa306b0e0f6ceb081
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071184B2

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