Methanesulfonyl chloride → HCID 11682865, compound

HRID 1350871Notes

Reaction equation

HRID 1350871 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11](=[O:24])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH3:9])=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:11]([NH:10][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:3][CH:4]=2)[CH3:9])=[O:24])=[CH:19][CH:18]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58640419HCID 58640419, compound

Product 1

HCID 11682865HCID 11682865, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a pyridine (5.0 ml) solution of N-[(1R)-1-(4-aminophenyl)ethyl]-2-(4-tert-butylphenoxy)acetamide (420 mg, 1.0 mmol), methanesulfonyl chloride (114 mg, 1.0 mmol) was added at 0° C. and the mixture was stirred for 3 hours at 0° C. The reaction mixture was then quenched with 2 M HCl and then crude products were extracted with methylene dichloride The organic layer was then washed with brine, dried over Na2SO4. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with methylene dichloride/ethylacetate=1/1 to furnish 120 mg (29% yield) of the title as a white solid.

Workup

  1. customThe reaction mixture was then quenched with 2 M HCl
  2. extractioncrude products were extracted with methylene dichloride The organic layer
  3. washwas then washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration
  6. customto separate solvent and sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto give a residue, which
  9. washeluted with methylene dichloride/ethylacetate=1/1
  10. customto furnish 120 mg (29% yield) of the title as a white solid

Sources & evidence

ORD record
ord-4a44b36fd8ad4e87a0155e4f5ca49065
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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