Reacción #47112

Ecuación de reacción

N,O-dimethylhydroxylamine hydrochloride

ammonium chloride

Z-L-phenylglycine

1,1′-carbonyldimidazole

→

product 482

Rendimiento 98.3%

(S)-[(N-Methoxy-N-methylcarbamoyl)phenylmethyl]carbamic acid benzyl ester

Rendimiento 98.3%

Disolventes

EtOAc

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture is stirred at rt overnight
2. 2
   Otrothe organic layer is separated
3. 3
   Lavadowashed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   OtroThe filtrate is evaporated

Procedimiento

To a solution of Z-L-phenylglycine (5.0 g, 17.5 mmol) in dichloromethane (35 mL) is added 1,1′-carbonyldimidazole (3.13 g, 19.3 mmol), and the solution is stirred at rt for 0.5 h. To the solution is added N,O-dimethylhydroxylamine hydrochloride (1.88 g, 19.3 mmol), and the mixture is stirred at rt overnight. To the reaction mixture is added ammonium chloride solution and EtOAc, and the organic layer is separated, washed with brine, dried (MgSO4), and filtered. The filtrate is evaporated to give 5.65 g of the product 482. 1H NMR (CDCl3) δ 7.50-7.20 (m, 10 H), 6.10 (d, 1 H), 5.78 (d, 1 H), 5.20-5.00 (m, 2 H), 3.43 (s, 3 H), 3.18 (s, 3 H); MS: m/z 329 (M++1).

Fuente