Reaktion #11104

Reaktionsgleichung

DCC

formic acid

intermediate 26a

(6S,8R)-alIyl-{8-amino-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

pyridine

→

intermediate 42a

Ausbeute 75.0%

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

Ausbeute 75.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   Extraktionextracted with chloroform (6×)
3. 3
   Trocknendried (Na2SO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigeIt was purified by SiO2 chromatography (gradient elution, 1–12% MeOH/CH2Cl2)

Vorschrift

To a solution of DCC (18.6 mg, 0.090 mmol) and formic acid (8.28 mg, 0.180 mmol) in CH2Cl2 that had been stirred at 0° C. for 10 min, was added intermediate 26a (30 mg, 0.045) in a solution of pyridine. The reaction was stirred at 0° C. for 15m then at rt for 2 h. The reaction mixture was concentrated in vacuo, then taken up in brine and extracted with chloroform (6×), dried (Na2SO4) and concentrated. It was purified by SiO2 chromatography (gradient elution, 1–12% MeOH/CH2Cl2) to afford 23.3 mg (75%) of intermediate 42a. MS (ESI) 692.2 (M+H+).

Quelle