Reaction #11087

Reaction equation

28d

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

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

HOAT

NaHCO3

EDCI

→

intermediate 28e

Yield 20.8%

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

Yield 20.8%

Solvents

EtOAc

CH2Cl2 DMF

Conditions

Workup

1. 1
   Washthe organic phase was washed with H2O, 1N HCl, H2O, and brine
2. 2
   DryingThe organic phase was dried (Na2SO4)
3. 3
   Concentrationconcentrated
4. 4
   OtherThe residue obtained
5. 5
   Otherwas purified by flash chromatography (75% EtOAc/hexanes)

Procedure

To a solution of 28d (172 mg, 0.420 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride (180 mg, 0.504 mmol) in 3.6 mL CH2Cl2/DMF (5:1) at 0° C., was added HOAT (113 mg, 0.588 mmol), NaHCO3 (141 mg, 1.68 mmol), and EDCI (113 mg, 0.588 mmol). The mixture was allowed to warm to rt and stir for 64 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 (75% EtOAc/hexanes) to afford 59 mg of intermediate 28e.

Source