Ethanol → (S)-N-Benzyl-N-methyl-2-[N-(b-butoxycarbonyl)-2-hydroxy-ethylamino]-3-phenyl-propionamide

HRID 1379967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379967
[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])(C)[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+].[CH2:33](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][CH:22]([CH2:25][CH3:33])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 53842533(S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Produkt 1

HCID 86751365(S)-N-Benzyl-N-methyl-2-[N-(b-butoxycarbonyl)-2-hydroxy-ethylamino]-3-phenyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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-fe9a3f58999641d3a633fa0dcc6da3c3
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672602

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