Réaction #11064

Équation de réaction

18a

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

aniline

HOAT

NaHCO3

EDCI

→

18b

(6S)-allyl-(4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl)-carbamic acid benzyl ester

Solvants

EtOAc

CH2Cl2 DMF

Conditions de réaction

Traitement

1. 1
   Lavagethe organic phase was washed with H2O, 1N HCl, H2O, and brine
2. 2
   SéchageThe organic phase was dried (Na2SO4)
3. 3
   Concentrationconcentrated
4. 4
   AutreThe residue obtained
5. 5
   Autrewas purified by flash chromatography (80 to 90% EtOAc/hexanes)

Mode opératoire

To a solution of 18a (5.50 g, 14.89 mmol) and aniline (1.93 mL, 22.3 mmol) in 75 mL 5:1 CH2Cl2/DMF at 0° C., was added HOAT (2.23 g, 16.4 mmol), NaHCO3 (2.50 g, 29.8 mmol), and EDCI (4.00 g, 20.8 mmol). The mixture was stirred and allowed to warm to rt over 72 h. The reaction was diluted with EtOAc and the organic phase was washed with H2O, 1N HCl, H2O, and brine. The organic phase was dried (Na2SO4) and concentrated. The residue obtained was purified by flash chromatography (80 to 90% EtOAc/hexanes) to afford 3.825 g (58%, 2 steps) of 18b as an off-white solid.

Source