Methanesulfonyl chloride → tert-butyl (3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

HRID 1350197Notes

Reaction equation

HRID 1350197 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][NH:25][CH3:26])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][N:25]([CH3:26])[S:28]([CH3:27])(=[O:30])=[O:29])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 16747948tert-butyl(3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate

Product 1

HCID 16748327tert-butyl (3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoateYield 75.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of tert-butyl(3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate (preparation 5) (300 mg, 0.82 mmol) in pyridine (2 ml) in a water bath was treated with methanesulphonylchloride (64 μl, 0.82 mmol) and stirred under a nitrogen atmosphere for 20 minutes. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with 2M HCl followed by brine. The organic extract was dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified on a silica column eluting with a solvent gradient of EtOAc:pentane (5:95) gradually changing to (30:70) to afford the title compound as a colourless oil (273 mg, 75%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 2M HCl
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified on a silica column
  9. washeluting with a solvent gradient of EtOAc:pentane (5:95)

Sources & evidence

ORD record
ord-9f32adc8f0184f1180966d52164e0345
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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