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

HRID 2084448Notes

Reaction equation

HRID 2084448 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:5][N:4]=1.N1C(C)=CC=CC=1C.[CH:34]([S:37](Cl)(=[O:39])=[O:38])([CH3:36])[CH3:35]>C(Cl)Cl>[CH:20]1([CH2:19][CH2:18][CH2:17][C@@H:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][NH:1][S:37]([CH:34]([CH3:36])[CH3:35])(=[O:39])=[O:38])[N:7]=2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 824082-Propanesulfonyl chlorideHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 16748329tert-butyl (3R)-6-cyclohexyl-3-(3-{[(isopropylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoateYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl (3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (216 mg, 0.61 mmol) and 2,6-lutidine (180 μl, 1.50 mmol) in DCM (3 ml) was treated with isopropanesulphonylchloride (100 μl, 0.90 mmol) and stirred at room temperature for 18 hours. Reaction was complete but it was left for 12 days before purification commenced. The reaction mixture was diluted with DCM and washed with 1M HCl (2×20 ml), sat. NaHCO3 solution and brine. The organic extract was dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified on a silica column eluting with a solvent gradient of pentane:EtOAc (90:10) gradually changing to (50:50) to afford the title compound as a colourless oil (157 mg, 56%).

Workup

  1. customReaction
  2. waitit was left for 12 days before purification
  3. washwashed with 1M HCl (2×20 ml), sat. NaHCO3 solution and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous 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 pentane:EtOAc (90:10)

Sources & evidence

ORD record
ord-0ce4c9dc5d134fecb45739e95b18ea4e
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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