Semicarbazide → t-Butyl N-Allyloxycarbonyl-4-amino-5-oxopentanoate semicarbazone

HRID 2230435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230435
[CH2:1]([O:4][C:5]([NH:7][CH:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O)=[O:6])[CH:2]=[CH2:3].C([O-])(=O)C.[Na+].[NH2:25][NH:26][C:27]([NH2:29])=[O:28]>CO>[CH2:1]([O:4][C:5]([NH:7][CH:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11](=[N:25][NH:26][C:27]([NH2:29])=[O:28])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:6])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 5196SemicarbazideHCID 517045Sodium AcetateHCID 18465646t-Butyl N-Allyloxycarbonyl-4-amino-5-oxopentanoate

Produkt 1

HCID 54326573t-Butyl N-Allyloxycarbonyl-4-amino-5-oxopentanoate semicarbazoneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 207a (2.39 g, 8.8 mmol), in MeOH (20 ml) was added sodium acetate (0.72 g, 8.8 mmol) and semicarbazide (0.98 g, 8.8 mmol) stirred overnight, concentrated and diluted with CH2Cl2 (100 ml), washed with water, dried and concentrated. Flash chromatography (2% MeOH in CH2Cl2) afforded 208a (2.10 g, 73%) as an oil: [α]D20 −21 (c 2.55°, CH2Cl2); 1H NMR (CDCl3) δ9.98 (1H, s), 7.27 (1H, d), 5.8 (1H, m), 5.5 (1H, d), 5.35-5.19 (2H, m), 4.58 (2H, m), 4.14 (1H, m), 2.37 (2H, t), 2.09 (1H, m), 2.0-1.75 (2H, m); Anal. Calcd for C14H24N4O5: C, 51.21; H, 7.37; N, 17.06. Found: C, 50.2; H, 7.3; N, 16.1.

Aufarbeitung

  1. concentrationconcentrated
  2. additiondiluted with CH2Cl2 (100 ml)
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-036a4bd431704092b580f83d59bd14a9
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423840B1

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