Trifluoroacetic acid → US9434719, 268 as TFA salt

HRID 57496Notes

Reaction equation

HRID 57496 reaction equation
C([O:5][C@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C@H:21]([C:23]2[S:27][C:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[N:25][CH:24]=2)[CH3:22])[N:15]=1)[CH3:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]2[S:27][C:23]([C@@H:21]([NH:20][C:16]3[N:15]=[C:14]([N:9]4[C@@H:8]([C@@H:6]([OH:5])[CH3:7])[CH2:12][O:11][C:10]4=[O:13])[CH:19]=[CH:18][N:17]=3)[CH3:22])=[CH:24][N:25]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90414586(R)-4-((S)-1-(tert-butoxy)ethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

Product 1

HCID 90414838US9434719, 268 as TFA saltYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing a stir bar and (R)-4-((S)-1-(tert-butoxy)ethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (82 mg, 0.16 mmol) was added DCM (1 mL) followed by the addition of TFA (1 mL). Resulting reaction mixture allowed to stir 30 min at RT. The volatiles were then removed and the residue neutralized by the addition of a saturated solution of NaHCO3. The aqueous mixture was then extracted with DCM. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated to a brown foam of (R)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((S)-1-hydroxyethyl)oxazolidin-2-one (61 mg, 0.14 mmol, 84% yield) which was used without further purification. LCMS m/z 446.2 (M+H)+, Rt 0.71 min.

Workup

  1. additionTo a round bottom flask containing a stir bar
  2. customResulting
  3. customreaction mixture
  4. customThe volatiles were then removed
  5. additionthe residue neutralized by the addition of a saturated solution of NaHCO3
  6. extractionThe aqueous mixture was then extracted with DCM
  7. washwashed with water, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-9ea056c571734e198840b8a429991b77
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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