تفاعل #11067

معادلة التفاعل

18f

(6S,8R)-3-(allyl-benzyloxycarbonyl-amino)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid

[(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester

HOAT

NaHCO3

EDCI

→

intermediate

المردود 90.0%

(6S,8R)-allyl-{8-azido-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamic acid benzyl ester

المردود 90.0%

المذيبات

EtOAc

CH2Cl2 DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine
2. 2
   تجفيفThe mixture was dried (Na2SO4)
3. 3
   تركيزconcentrated

الإجراء التجريبي

To a solution of 18f (270 mg, 0.636 mmol) and [(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester (272 mg, 0.763 mmol) in 6 mL CH2Cl2/DMF (5:1) at 0° C., were added HOAT (95 mg, 0.700 mmol), NaHCO3 (187 mg, 2.23 mmol), and EDCI (171 mg, 0.890 mmol). The mixture was allowed to warm to rt and stir for 15 h. The mixture was diluted with EtOAc, washed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine. The mixture was dried (Na2SO4) and concentrated to afford 393 mg (90%) of intermediate 18 g.

المصدر