Methanesulfonyl chloride → (S)-1-((R)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)-2-oxooxazolidin-4-yl)ethyl methanesulfonate

HRID 57497ノート

反応式

HRID 57497 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C@@H:13]([NH:15][C:16]3[N:21]=[C:20]([N:22]4[C@@H:26]([C@@H:27]([OH:29])[CH3:28])[CH2:25][O:24][C:23]4=[O:30])[CH:19]=[CH:18][N:17]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:40][S:41]([O:29][C@H:27]([C@H:26]1[CH2:25][O:24][C:23](=[O:30])[N:22]1[C:20]1[CH:19]=[CH:18][N:17]=[C:16]([NH:15][C@H:13]([C:10]2[S:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:12][CH:11]=2)[CH3:14])[N:21]=1)[CH3:28])(=[O:43])=[O:42]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 90414838US9434719, 268 as TFA salt

生成物 1

HCID 90414700(S)-1-((R)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)-2-oxooxazolidin-4-yl)ethyl methanesulfonate収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a round bottom flask with stir bar was added (R)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((S)-1-hydroxyethyl)oxazolidin-2-one (19 mg, 0.04 mmol) followed by the addition of DCM (1 mL) under nitrogen. Mixture was cooled to 0° C. in a ice/water bath. To this cold solution was added DIEA (0.03 mL, 0.17 mmol) followed by the addition of methanesulfonyl chloride (10 μL, 0.13 mmol). Reaction mixture stirred for 1 hr at 0° C. The reaction mixture was then quenched with water and diluted with DCM. Phases partitioned and the aqueous phase extracted with DCM. Organic layers combined and washed with brine, dried (Na2SO4), filtered and concentrated to afford a orange residue of (S)-1-((R)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)-2-oxooxazolidin-4-yl)ethyl methanesulfonate (21 mg, 0.04 mmol, 94% yield). LCMS m/z 524.2 (M+H)+, Rt 0.75 min.

後処理

  1. customReaction mixture
  2. stirringstirred for 1 hr at 0° C
  3. customThe reaction mixture was then quenched with water
  4. additiondiluted with DCM
  5. customPhases partitioned
  6. extractionthe aqueous phase extracted with DCM
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-b5e1e7580ed1405797d3eb40da12f779
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

反応ノート

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