Reacción #314336

Ecuación de reacción

[(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

[(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

(S)-2-tert-butoxycarbonylamino-3-methyl-butyric acid

4-iodo-benzene-1,2-diamine

diisopropylethyl amine

O-benzotriazol-1-yl-N,N, N′,N′-tetramethyluronium

sodium carbonate

→

(R)-5-[4-(2-Hydroxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-methyl-propyl]-imidazolidine-2,4-dione

Disolventes

N,N-dimethylformamide

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture was extracted with ethyl acetate
2. 2
   Lavadothe organic layer was washed with aqueous sodium carbonate solution and brine
3. 3
   Secadodried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   Otroto give

Procedimiento

To the solution of (S)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (0.33 g, 1.5 mmol), 4-iodo-benzene-1,2-diamine (0.35 g, 1.5 mmol) and diisopropylethyl amine (0.8 mL, 4.5 mmol) in N,N-dimethylformamide (6 mL) was added dropwise a solution of O-benzotriazol-1-yl-N,N, N′,N′-tetramethyluronium hexaflurorophosphate (0.71 g, 1.75 mmol) N,N-dimethylformamide (2 mL). The reaction mixture was stirred for 12 hours at room temperature. After adding aqueous sodium carbonate solution, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with aqueous sodium carbonate solution and brine, dried over sodium sulfate, filtered, and concentrated to give a mixture of regioisomers, [(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester and [(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (0.65 g, 100%).

Fuente