Reaktion #969856

Reaktionsgleichung

1-(tert-Butoxycarbonylamino)-4-ethoxy-4-oxobutane-2-sulfonic acid

lithium hydroxide monohydrate

→

title compound

Ausbeute 90.0%

4-(tert-butoxycarbonylamino)-3-sulfobutanoic acid

Ausbeute 90.0%

Lösungsmittel

THF H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated
2. 2
   Sonstigepurified on C-18 column (2×30 cm)
3. 3
   Wascheneluted with from 100% water to 10% methanol in water

Vorschrift

1-(tert-Butoxycarbonylamino)-4-ethoxy-4-oxobutane-2-sulfonic acid (402 mg, 1.29 mmol) in the mixture of THF/H2O (1:2, 60 ml) was added lithium hydroxide monohydrate (2.0 g, 47.6 mmol). The mixture was stirred under Ar overnight, concentrated, purified on C-18 column (2×30 cm) eluted with from 100% water to 10% methanol in water to afford 328 mg (90%) of the title compound. 1H NMR (DMSO), 6.78 (s, 1H), 4.03 (m, 1H), 3.57 (dd, 1H, J=4.2, 13.4 Hz), 3.41 (m, 1H), 2.89 (m, 1H), 2.61 (m, 1H), 1.39 (s, 9H); 13C NMR 174.21, 155.82, 79.85, 59.95, 42.06, 32.52, 28.88, 14.55; ESI MS 281.8 (M−H);

Quelle