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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
Notes
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Reaction equation

HRID 57499 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 68983Trimethylphosphine2×HCID 90414877(S)-4-((R)-1-azidoethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

Product 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-oneYield 15.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9656e271c98e45ed938035bf9a753ab9
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434719B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes