(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester → (2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

HRID 990324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990324
C([O:8][C:9](=[O:25])[C@@H:10]([NH:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>C1COCC1.[Pd]>[N:18]1([C:16]([NH:15][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:25])=[O:8])=[O:17])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

4

Edukt 1

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

Produkt 1

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester (38.5 g. 111 mmol) in 600 mL of THF was hydrogenated at 50 psi over 20% Pd/C (2.00 g) for 17 minutes. The reaction mixture was filtered through celite and concentrated to dryness. The residue was heated in 50 mL of hexane. The resulting suspension was cooled and the solid collected by filtration and washed with hexane. The solid was dried at room temperature under vacuum to give the title compound as a white solid (26.6 g, 93%); mp 88-89° C.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated to dryness
  3. temperatureThe residue was heated in 50 mL of hexane
  4. temperatureThe resulting suspension was cooled
  5. filtrationthe solid collected by filtration
  6. washwashed with hexane
  7. customThe solid was dried at room temperature under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5ec5199833f044679ddfd3d15a51d4a8
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458781B1

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