p-Toluenesulfonic acid → HCID 45110757, compound

HRID 386916Notes

Reaction equation

HRID 386916 reaction equation
[CH3:1][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18](=[O:33])[C:19]([CH3:32])([S:21]([CH:24]([CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH3:25])(=[O:23])=[O:22])[CH3:20])[O:14][N:13]=1)([CH3:11])[CH2:3][O:4]C1CCCCO1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CCOCC>[OH:4][CH2:3][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18](=[O:33])[C:19]([CH3:32])([S:21]([CH:24]([CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH3:25])(=[O:23])=[O:22])[CH3:20])[O:14][N:13]=1)([CH3:11])[CH3:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59253277HCID 59253277, compound

Product 1

HCID 45110757HCID 45110757, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A solution of 100 mg (0.24 mmol) of N-{3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-2-methyl-2-[1-(tetrahydro-pyran-4-yl)-ethanesulfonyl]-propionamide in DCM/ethanol (1/1, 10 mL) is treated with 145 mg (0.48 mmol) of MP-TsOH resin (loading 3.3 mmol/g) at room temperature for 18 h. The resin is removed by filtration and washed with DCM (10 mL) and methanol (10 mL). The combined filtrates are concentrated under reduced pressure and the resulting residue is slurried in heptanes/ethyl acetate (7/3) to yield 74 mg of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-2-[1-(tetrahydro-pyran-4-yl)-ethanesulfonyl]-propionamide. Yield 87%; ES-MS: m/z 403 [M+H].

Workup

  1. customThe resin is removed by filtration
  2. washwashed with DCM (10 mL) and methanol (10 mL)
  3. concentrationThe combined filtrates are concentrated under reduced pressure

Sources & evidence

ORD record
ord-92a7e24480954adea5b4ec21c9a44d28
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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