Sodium borohydride → (S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-hydroxy-ethylamino]-3-phenyl-propionamide

HRID 235543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235543
[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH:27]=[O:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH2:27][OH:28])[C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 53842533(S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Produkt 1

HCID 54174094(S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-hydroxy-ethylamino]-3-phenyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine (S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide (5.0 mmol) and sodium borohydride (5.0 mmol) in ethanol (20 mL). Stir for 16 hours. Concentrate in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with 0.5M hydrochloric acid solution and water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Aufarbeitung

  1. concentrationConcentrate in vacuo
  2. customto obtain a residue
  3. extractionextract with 0.5M hydrochloric acid solution and water
  4. customSeparate the layers
  5. dry with materialdry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-60c3190e76c34543b4512c29e6c4bbc4
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597845

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