Reaktion #1275912

Reaktionsgleichung

[(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-ethoxy-phosphinoyl]-acetic acid ethyl ester

NaOH

→

[(1-Benzyloxycarbonylamino-2-vinyl-cyclopropyl)-ethoxy-phosphinoyl]-acetic acid

Ausbeute 69.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Einengenconcentrated
3. 3
   workup.ADDITIONdiluted with H2O (10 mL)
4. 4
   Waschenwashed with ethyl acetate
5. 5
   Extraktionextracted with ethyl acetate (×2)
6. 6
   WaschenThe organic extracts were washed with H2O
7. 7
   Trocknendried (MgSO4)
8. 8
   Einengenconcentrated

Vorschrift

A solution of [(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-ethoxy-phosphinoyl]-acetic acid ethyl ester (352 mg, 0.89 mmol) in THF (3 mL) was stirred at 0° C. as 1 N NaOH (980 μL, 0.98 mmol) was added. The solution was stirred overnight at r.t. and then concentrated, diluted with H2O (10 mL) and washed with ethyl acetate. The aqueous layer was acidified with 1 N HCl (5 mL) and extracted with ethyl acetate (×2). The organic extracts were washed with H2O, dried (MgSO4) and concentrated to yield [(1-Benzyloxycarbonylamino-2-vinyl-cyclopropyl)-ethoxy-phosphinoyl]-acetic acid (224 mg, 69%). 1H NMR (300 MHz, CDCl3): d 7.34 (s, 5H), 5.91 (m, 2H), 5.20 (m, 2H), 4.21 (m, 2H), 3.11 (m, 2H), 2.30 (m, 1H), 2.03 (m, 1H), 1.85 (m, 2H), 1.70 (m, 2H), 1.58 (m, 2H), 1.38 (m, 2H), 1.25 (m, 3H). 31P (121.4 MHz, CDCl3): 45.109, 41.119, 40.965, 39.514

Quelle