Trifluoroacetic acid → US9434719, 268 as TFA salt

HRID 57496ノート

反応式

HRID 57496 の反応式
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

参加物

4

反応物 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

生成物 1

HCID 90414838US9434719, 268 as TFA salt収率 87.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ea056c571734e198840b8a429991b77
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

反応ノート

読み込み中…