Reaktion #632018

Reaktionsgleichung

product

cyclopropanesulfonic acid (1-(R)-tert-butoxycarbonylamino-2-(S)-vinylcyclopropanecarbonyl)amide

dichloromethane

→

desired product

cyclopropanesulfonic acid (1-(R)-amino-2-(S)-vinyl-cyclopropanecarbonyl)amide HCl salt

Lösungsmittel

TFA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatiles were removed in vacuo
2. 2
   Einengenconcentrated in vacuo
3. 3
   SonstigeThe resulting mixture was triturated from pentane
4. 4
   Filtrationfiltered

Vorschrift

A solution of the product of Step 2 (3.5 g, 10.6 mmol) in dichloromethane (35 mL) and TFA (32 mL) was stirred at room temperature for 1.5 hours. The volatiles were removed in vacuo and the residue was suspended in 1N HCl in diethyl ether (20 mL) and concentrated in vacuo. This procedure was repeated once. The resulting mixture was triturated from pentane and filtered to provide the desired product as a hygroscopic, off-white solid (2.60 g, 92%). 1H NMR: (DMSO-d6) δ 1.01-1.15 (m, 4H), 1.69-1.73 (m, 1H), 1.99-2.02 (m, 1H), 2.38 (q, J=9 Hz, 1H), 2.92-2.97 (m, 1H), 5.20 (d, J=11 Hz, 1H), 5.33 (d, J=17 Hz, 1H), 5.52-5.59 (m, 1H), 9.17 (br s, 3H) LC-MS (retention time: 0.24 minutes, method B), MS m/z 231 (M++H).

Quelle