tert-Butyl 4-oxopiperidine-1-carboxylate → (S)-2-(benzyloxycarbonylamino)-5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pentanoic acid

HRID 407925

Reaktionsgleichung

Reaktionsgleichung von HRID 407925
[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:6]([OH:8])=[O:7].O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.C([BH3-])#N.[Na+]>C1COCC1.O>[CH2:13]([O:12][C:10]([NH:9][C@@H:5]([CH2:4][CH2:3][CH2:2][NH:1][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)[C:6]([OH:8])=[O:7])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 7010490N-alpha-Benzyloxycarbonyl-L-ornithine

Produkt 1

HCID 58787298(S)-2-(benzyloxycarbonylamino)-5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-5-amino-2-(benzyloxycarbonylamino)pentanoic acid (50 g, 188 mmol) was dissolved in THF (800 mL) and water (100 mL). Tert-butyl 4-oxopiperidine-1-carboxylate (37 g, 188 mmol) was added and the reaction was stirred for 1 hour. The reaction was cooled to 0° C. and sodium cyanoborohydride (12 g, 188 mmol) was added and the reaction stirred at ambient temperature overnight. The reaction was concentrated to provide (S)-2-(benzyloxycarbonylamino)-5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pentanoic acid, which was used directly in the next step.

Aufarbeitung

  1. stirringthe reaction stirred at ambient temperature overnight
  2. concentrationThe reaction was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2574fbdf2f8f41c9bbe86b41ad067089
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

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