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 57497Notes

Reaction equation

HRID 57497 reaction equation
[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]

Participants

5

Reactant 3

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

Product 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 methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b5e1e7580ed1405797d3eb40da12f779
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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