Reaction #324425

Reaction equation

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

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherto quench
3. 3
   Otherthe reaction
4. 4
   OtherThe two phases were separated
5. 5
   ExtractionThe aqueous phase was extracted by EtOAc twice
6. 6
   Washthe combined organic phase was washed by brine
7. 7
   Dryingdried over sodium sulfate
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe residue was chromatographed on silica gel
10. 10
    Washeluting with EtOAc

Procedure

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.

Source