Reaktion #2444258

Reaktionsgleichung

(S)-tert-butyl 2,2,4-trimethyl-4-(3-(4-(octyloxy)-3-(trifluoromethyl)-phenyl)-3-oxo-propanoyl)oxazolidine-3-carboxylate

hydroxylamine hydrochloride

TFA DCM

→

title compound

(S)-2-Amino-2-(3-(4-(octyloxy)-3-(trifluoromethyl)phenyl)isoxazol-5-yl)propan-1-ol

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigecondensed
2. 2
   SonstigeAfter removal of excess amount of TFA and DCM
3. 3
   Sonstigethe crude product was purified by prep

Vorschrift

The solution of (S)-tert-butyl 2,2,4-trimethyl-4-(3-(4-(octyloxy)-3-(trifluoromethyl)-phenyl)-3-oxo-propanoyl)oxazolidine-3-carboxylate (27 mg, 0.05 mmol, 1.0 equiv) and hydroxylamine hydrochloride (6.6 mg, 0.10 mmol, 2.0 equiv) in pyridine (0.5 mL) was stirred at 60° C. for 2 days. The reaction was condensed and the residue was treated with 20% TFA-DCM for 30 min. After removal of excess amount of TFA and DCM, the crude product was purified by prep. HPLC and afforded the title compound as mono-TFA salt (6.0 mg). MS (ESI, M+H+)=415.0; 1H NMR (400 MHz, CD3OD) δ 8.06 (s, 1H), 8.04 (d, 1H, J=9.6 Hz), 7.31 (d, 1H, J=9.6 Hz), 7.03 (s, 1H), 4.16 (t, 2H, J=6.0 Hz), 4.01, 3.83 (AB, 2H, J=12.0 Hz), 1.87-1.80 (m, 2H), 1.75 (s, 3H), 1.56-1.47 (m, 2H), 1.40-1.32 (m, 8H), 0.91 (t, 3H, J=7.2 Hz).

Quelle