Reaktion #2444247

Reaktionsgleichung

(R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid

HATU

diisopropylethyl amine

4-(octyloxy)-3-(trifluoromethyl)benzohydrazide

4-(Octyloxy)-3-(trifluoromethyl)benzohydrazide

→

title compound

Ausbeute 92.1%

(S)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate

Ausbeute 92.1%

Lösungsmittel

CH2Cl2 DMF

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated under vacuum
2. 2
   workup.ADDITIONThe residue was diluted with ethyl acetate (20 mL)
3. 3
   Waschenwashed with water (5 mL), brine (2×10 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   EinengenThe organic layer was concentrated in vacuo
6. 6
   Sonstigechromatographed on a silica gel column (ethyl acetate-hexane, 0-33%, as eluent)

Vorschrift

(R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid (4) (210 mg, 0.81 mmol) was stirred with HATU (372 mg, 0.98 mmol) and diisopropylethyl amine (DIEA) (0.705 mL, 4.1 mmol) in CH2Cl2-DMF (2:1, 6 mL) for 10 min followed by addition of 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (12a) (270 mg, 0.81 mmol) in CH2Cl2 (2 mL). The reaction was stirred at room temperature for 1 hour and then was concentrated under vacuum. The residue was diluted with ethyl acetate (20 mL) and washed with water (5 mL), brine (2×10 mL) and dried over Na2SO4. The organic layer was concentrated in vacuo and chromatographed on a silica gel column (ethyl acetate-hexane, 0-33%, as eluent) to afford the title compound (428 mg, 82% yield). MS (ESI): 573.84 (MH+); 1H NMR (400 MHz, CDCl3) δ 9.43 (br, 2H), 8.06 (d, 1H, J=2.0 Hz), 7.94 (dd, 1H, J=8.8 Hz, J=2.0 Hz), 6.96 (d, 1H, J=8.8 Hz), 4.52 (br, 1H), 4.07 (t, 2H, J=6.4 Hz), 3.76 (br, 1H), 1.82 (m, 2H), 1.67 (s, 6H), 1.57 (s, 3H), 1.51 (s, 9H), 1.51-1.43 (m, 4H), 1.38-1.24 (m, 6H), 0.88 (t, 3H, J=7.2 Hz).

Quelle