반응 #85777

반응 방정식

trimethylphosphine

(S)-4-((R)-1-azidoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

TFA

trimethylphosphine

→

(S)-4-((R)-1-aminoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

수율 15.3%

용매

THF

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   workup.STIRRINGto stir 2 hr at RT
3. 3
   workup.STIRRINGto stir 1.5 hr at RT
4. 4
   기타Reaction
5. 5
   기타was quenched by the addition of a saturated solution of NH4Cl and EtOAc
6. 6
   기타The phases were partitioned
7. 7
   추출aqueous phase extracted with EtOAc
8. 8
   세척washed with brine
9. 9
   건조dried (Na2SO4)
10. 10
    여과filtered
11. 11
    농축concentrated to a yellow residue
12. 12
    workup.DISSOLUTIONResidue dissolved in DMSO
13. 13
    기타purified by reverse phase HPLC
14. 14
    온도frozen

실험 절차

To a round bottom flask containing (S)-4-((R)-1-azidoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (14 mg, 0.03 mmol) and stir bar was added THF (1 mL) and trimethylphosphine (0.06 mL, 0.06 mmol, 1.0 M in THF). The resulting reaction mixture allowed to stir 2 hr at RT. A second addition of trimethylphosphine (0.06 mL, 0.06 mmol) occurred and the mixture allowed to stir 1.5 hr at RT. Reaction was quenched by the addition of a saturated solution of NH4Cl and EtOAc. The phases were partitioned and aqueous phase extracted with EtOAc. Organic phases combined and washed with brine, dried (Na2SO4), filtered and concentrated to a yellow residue. Residue dissolved in DMSO and purified by reverse phase HPLC. Product fractions combined, frozen and lyopholyzed to afford (S)-4-((R)-1-aminoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (2.6 mg, 4.60 μmol, 15% yield) as a TFA salt.

출처