反应 #324425

反应方程式

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

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   其他to quench
3. 3
   其他the reaction
4. 4
   其他The two phases were separated
5. 5
   萃取The aqueous phase was extracted by EtOAc twice
6. 6
   洗涤the combined organic phase was washed by brine
7. 7
   干燥dried over sodium sulfate
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他The residue was chromatographed on silica gel
10. 10
    洗涤eluting with EtOAc

实验过程

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.

来源