Methanesulfonyl chloride → (2R)-N-(4-cyanophenyl)-2-hydroxy-2-[(2R)-4-[4-(methanesulfonamido)phenyl]-3-oxo morpholin-2-yl]acetamide

HRID 876574Notes

Reaction equation

HRID 876574 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([C@@H:14]([OH:26])[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)=[O:16])[C:9]2=[O:27])=[CH:4][CH:3]=1.[S:28](Cl)([CH3:31])(=[O:30])=[O:29]>CN(C=O)C.N1C=CC=CC=1.O>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C@H:14]([OH:26])[C@H:10]2[O:11][CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:3][CH:4]=3)[C:9]2=[O:27])=[CH:19][CH:20]=1)#[N:25]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67032877(2R)-2-[(2R)-4-(4-aminophenyl)-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamide

Product 1

HCID 67223574(2R)-N-(4-cyanophenyl)-2-hydroxy-2-[(2R)-4-[4-(methanesulfonamido)phenyl]-3-oxo morpholin-2-yl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21954950Dimethylformamide pyridineSolvent

Procedure

To a solution of compound 26-5 (70 mg) in DMF-pyridine (2 mL-2 mL), was added mesyl chloride (16.3 microL). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with water then it was extracted with EtOAc. The extract was washed with water, 1N HCl and brine. The organic layer was dried with anhyd. Na2SO4 and the solvent was removed under reduced pressure to obtain compound 28-1 (30 mg) as a pale yellow amorphous solid.

Workup

  1. extractionit was extracted with EtOAc
  2. washThe extract was washed with water, 1N HCl and brine
  3. customThe organic layer was dried with anhyd
  4. customNa2SO4 and the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3bdc7ed7a6ac46cdad935d0b7923e0fa
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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