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 57497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57497
[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]

Komponenten

5

Edukt 3

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

Produkt 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 methanesulfonateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b5e1e7580ed1405797d3eb40da12f779
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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