p-Toluenesulfonic acid → HCID 45111497, compound

HRID 386902Notes

Reaction equation

HRID 386902 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([S:11]([C:14]([CH3:36])([CH3:35])[C:15]([NH:17][C:18]2[O:22][N:21]=[C:20]([C:23]([CH3:34])([C@@H:25]([O:27]C3CCCCO3)[CH3:26])[CH3:24])[CH:19]=2)=[O:16])(=[O:13])=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3].CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.O>[OH:27][C@@H:25]([CH3:26])[C:23]([C:20]1[CH:19]=[C:18]([NH:17][C:15](=[O:16])[C:14]([S:11]([CH:8]2[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:10][CH2:9]2)(=[O:12])=[O:13])([CH3:36])[CH3:35])[O:22][N:21]=1)([CH3:34])[CH3:24]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59253165HCID 59253165, compound

Product 1

HCID 45111497HCID 45111497, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 192 mg (0.35 mmol) of 2-(1-methanesulfonylpiperidine-4-sulfonyl)-2-methyl-N-{3-[(3S)-2-methyl-3-(oxan-2-yloxy)butan-2-yl]-1,2-oxazol-5-yl}propanamide in DCM/methanol (1/1, 4 mL) is treated with 241 mg (1.40 mmol) of MP-TsOH resin (loading 3.3 mmol/g) at room temperature for 18 h. The resin is removed by filtration and washed alternating with DCM and methanol. The combined filtrates are concentrated under reduced pressure and the resulting residue is purified by column chromatography (silica, eluent: heptanes, 50-100% ethyl acetate) to yield 163 mg of N-{3-[(3S)-3-hydroxy-2-methylbutan-2-yl]-1,2-oxazol-5-yl}-2-(1-methanesulfonylpiperidine-4-sulfonyl)-2-methylpropanamide. Yield 78%; ES-MS: m/z 466 [M+H]

Workup

  1. customThe resin is removed by filtration
  2. washwashed
  3. concentrationThe combined filtrates are concentrated under reduced pressure
  4. customthe resulting residue is purified by column chromatography (silica, eluent: heptanes, 50-100% ethyl acetate)

Sources & evidence

ORD record
ord-5a3d265b1f9e498face759708be67632
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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