Reaktion #11097

Reaktionsgleichung

tert-butyl bromoacetate

Intermediate 18c

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

LiHMDS

→

intermediate 38a

Ausbeute 59.0%

(6R,8S)-[3-(allyl-benzyloxycarbonyl-amino)-8-methyl-4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl]-acetic acid tert-butyl ester

Ausbeute 59.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to −40° C. over 20 min
2. 2
   Sonstigequenched with NH4Cl
3. 3
   workup.ADDITIONThe reaction mixture was diluted with EtOAc
4. 4
   Waschenwashed with H2O, brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeIt was purified by SiO2 chromatography (50% EtOAc/hexanes)

Vorschrift

To Intermediate 18c (495.7 mg, 1.08 mmol) in THF at −78° C. was added LiHMDS (2.268 mL, 2.268 mmol) dropwise. After 10 min, tert-butyl bromoacetate was added and the mixture was stirred at −78° C. for 20 min. It was allowed to warm to −40° C. over 20 min, then quenched with NH4Cl. The reaction mixture was diluted with EtOAc, then washed with H2O, brine, dried (Na2SO4) and concentrated. It was purified by SiO2 chromatography (50% EtOAc/hexanes) to afford 367.9 mg (59%) of intermediate 38a.

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