Reaktion #969851

ord-330b3628d6254f7b93c405ba3bcb6a2e

Reaktionsgleichung

[N-]=[N+]=NCC(CC(=O)O)S(=O)(=O)O
4-azido-3-sulfobutanoic acid
NCC(CC(=O)O)S(=O)(=O)O
4-amino-3-sulfobutanoic acid
Ausbeute 95.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered through celite
  2. 2
    Sonstigeevaporated

Vorschrift

In a 500 ml of hydrogenation bottle was added 4-azido-3-sulfobutanoic acid (3.00 g, 14.35 mmol), 150 ml of methanol and 0.32 g of Pd/C (10% Pd, 50% wet). After sucked out air, 30 psi of H2 was conducted, and the mixture was shaken overnight, filtered through celite, evaporated, and coevaporated with dry EtOH to afford about 2.50 g (95%) of 4-amino-3-sulfobutanoic acid. 1H NMR (CD3OD) 3.24 (m, 1H), 3.17 (m, 1H), 2.90 (dd, 1H, J=2.6, 16.5 Hz), 2.33 (dd, 1H, J=10.1, 16.5 Hz), ESI MS m/z−181.60 (M−H). The resulted compound was unstable and was used directly without further purification.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236319B2uspto-grants-2012_08