تفاعل #11083

معادلة التفاعل

intermediate 25a

(S)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

[(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester

NaHCO3

HOAT

EDCI

→

intermediate 25b

المردود 79.2%

benzyl (S)-{6-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzylcarbamoyl]-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamate

المردود 79.2%

المذيبات

EtOAc

CH2Cl2 DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلThe organic phase was washed with H2O, 1N HCl, H2O, and sat. NaHCO3, and brine
2. 2
   تجفيفdried (Na2SO4) and brine
3. 3
   أخرىThe crude residue was triturated with Et2O

الإجراء التجريبي

To a solution of intermediate 25a (0.281 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester (84 mg, 0.337 mmol) in 3 mL 5:1 CH2Cl2/DMF at 0° C., were added NaHCO3 (59 mg, 0.703 mmol), HOAT (42.1 mg, 0.309 mmol), and EDCI (75.5 mg, 0.393 mmol). The mixture was allowed to warm to rt and stir 20 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, and sat. NaHCO3, and brine, dried (Na2SO4) and brine. The crude residue was triturated with Et2O to afford 160 mg (79%) of intermediate 25b as a white solid. MS (ESI) 719.4 (M+H+).

المصدر