Реакция #324425

Уравнение реакции

water MeOtBu

Water

title compound

tert-butyl (S)-1-((S)-1-((2S,4S)-4-azido-2-((R)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Ph3P

→

title compound

tert-butyl (S)-1-((S)-1-((2S,4S)-4-amino-2-((R)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Другоеto quench
3. 3
   Другоеthe reaction
4. 4
   ДругоеThe two phases were separated
5. 5
   ЭкстракцияThe aqueous phase was extracted by EtOAc twice
6. 6
   Промывкаthe combined organic phase was washed by brine
7. 7
   Сушкаdried over sodium sulfate
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   ДругоеThe residue was chromatographed on silica gel
10. 10
    Промывкаeluting with EtOAc

Методика

To a solution of the title compound of Example 3 (1.7 g, 2.9 mmol) in 10.6 mL dry THF was added Ph3P (765 mg, 2.9 mmol) at room temperature. Water (78.3 μL, 4.35 mmol) was added drop wise and the reaction mixture was allowed to stir for 16 hours at room temperature. A 1:1 mixture of water/MeOtBu was added to quench the reaction. The two phases were separated. The aqueous phase was extracted by EtOAc twice, and then the combined organic phase was washed by brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with EtOAc, the 5% to 15% MeOH/methylene chloride to give the title compound as a white foam-like solid. 1H NMR (CDCl3): consistent with proposed structure.

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