Reaktion #219337

Reaktionsgleichung

acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester

Z-dehydroalanine methyl ester

sodium bicarbonate

→

title compound

Ausbeute 69.0%

3-(2-Acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-phenyl)-2-benzyloxycarbonylamino-acrylic acid methyl ester

Ausbeute 69.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   Temperaturwas heated
3. 3
   Temperaturat reflux for 3.75 hours
4. 4
   Filtrationthen filtered through a plug of silica gel eluting 70% ethyl acetate-hexanes (500 mL)
5. 5
   EinengenFiltrate was concentrated in vacuo

Vorschrift

Palladium (II) acetate (105 mg, 0.43 mmol) was added to a mixture of acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester (2.89 g, 7.1 mmol), Z-dehydroalanine methyl ester (2.20 g, 9.4 mmol), tetrabutylammonium chloride hydrate (2.70 g, 9.7 mmol), and sodium bicarbonate (1.80 g, 21.4 mmol) in THF (100 mL). Reaction was heated at reflux for 3.75 hours. Mixture was cooled to room temperature then filtered through a plug of silica gel eluting 70% ethyl acetate-hexanes (500 mL). Filtrate was concentrated in vacuo. Silica gel chromatography afforded the title compound as a yellow solid in 69% yield. 1H NMR (300 MHz, CDCl3): δ=7.79 (d, J=8.4, 1H), 7.42 (s, 1H), 7.27 (m, 6H), 6.30 (s, 1H), 5.11 (s, 2H), 5.02 (s, 2H), 3.81 (s, 3H), 2.21 (s, 3H), 2.02 (s, 3H), 1.51 (s, 9H). MS m/e (M−H)−=511.0.

Quelle