Hydrazine → tert-butyl N-((1S)-1-(hydrazinecarbonyl)ethyl)carbamate

HRID 57404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57404
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:14])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][NH2:16]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH3:14])[C:10]([NH:15][NH2:16])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 9321Hydrazine2×HCID 10856577Boc-L-alanine methyl ester

Produkt 1

HCID 10241974tert-butyl N-((1S)-1-(hydrazinecarbonyl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)propanoate (1.00 g, 4.92 mmol) and hydrazine (0.23 mL, 1.5 equiv) in THF (8 mL) was heated in a sealed tube at 72° C. for 15 hours. Additional hydrazine (0.23 mL, 1.5 equiv) was added and heating was continued for another 21 hours. The reaction was then cooled to room temperature and concentrated in vacuo to give crude (S)-tert-butyl(1-hydrazinyl-1-oxopropan-2-yl)carbamate (1 g, white solid), which was used without purification. 1H NMR (400 MHz, CDCl3) δ 4.20 (m, 1H), 1.44 (s, 9H), 1.36 (d, J=7.1 Hz, 3H).

Aufarbeitung

  1. temperatureheating
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-af3f2e06c332425aab8953dc44bfeb70
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

Notizen zur Reaktion

Wird geladen…