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

HRID 57499
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HRID 57499 반응식
[N:1]([C@@H:4]([C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C@H:19]([C:21]2[S:25][C:24]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:23][CH:22]=2)[CH3:20])[N:13]=1)[CH3:5])=[N+]=[N-].CP(C)C.C(O)(C(F)(F)F)=O>C1COCC1>[NH2:1][C@@H:4]([C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C@H:19]([C:21]2[S:25][C:24]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)=[N:23][CH:22]=2)[CH3:20])[N:13]=1)[CH3:5]
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 68983Trimethylphosphine2회HCID 90414877(S)-4-((R)-1-azidoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

생성물 1

HCID 86269827(S)-4-((R)-1-aminoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one수율 15.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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.

후처리

  1. customThe resulting reaction mixture
  2. stirringto stir 2 hr at RT
  3. stirringto stir 1.5 hr at RT
  4. customReaction
  5. customwas quenched by the addition of a saturated solution of NH4Cl and EtOAc
  6. customThe phases were partitioned
  7. extractionaqueous phase extracted with EtOAc
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated to a yellow residue
  12. dissolutionResidue dissolved in DMSO
  13. custompurified by reverse phase HPLC
  14. temperaturefrozen

출처 및 근거

ORD 기록
ord-9656e271c98e45ed938035bf9a753ab9
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434719B2

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