Reaktion #11087

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 20.8%

Lösungsmittel

EtOAc

CH2Cl2 DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic phase was washed with H2O, 1N HCl, H2O, and brine
2. 2
   TrocknenThe organic phase was dried (Na2SO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue obtained
5. 5
   Sonstigewas purified by flash chromatography (75% EtOAc/hexanes)

Vorschrift

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.

Quelle