p-Toluenesulfonic acid → HCID 59267935, compound

HRID 1809442Notes

Reaction equation

HRID 1809442 reaction equation
[CH3:1][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18](=[O:34])[C:19]([S:22]([CH2:25][CH:26]2[CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28][CH2:27]2)(=[O:24])=[O:23])([CH3:21])[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:34])[C:19]([S:22]([CH2:25][CH:26]2[CH2:27][CH2:28][CH:29]([O:32][CH3:33])[CH2:30][CH2:31]2)(=[O:24])=[O:23])([CH3:21])[CH3:20])[O:14][N:13]=1)([CH3:1])[CH3:11]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59267986HCID 59267986, compound

Product 1

HCID 59267935HCID 59267935, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A solution of 1.3 g (2.6 mmol) of N-{3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-2-(4-methoxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide in DCM/methanol (1/1, 20 mL) is treated with 1.58 g (5.2 mmol) of MP-TsOH resin (loading 3.3 mmol/g) at room temperature for 36 h. The resin is removed by filtration and washed alternating with DCM (10 mL) and methanol (10 mL) twice. The combined filtrates are concentrated under reduced pressure and the resulting residue is purified by column chromatography (Isolute SCX-2, eluent: DCM, 10% ethyl acetate) to yield 0.41 g of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-(4-methoxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide. Yield 38%; ES-MS: m/z 417 [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 (Isolute SCX-2, eluent: DCM, 10% ethyl acetate)

Sources & evidence

ORD record
ord-cef7c490d2dd41c187b1b4df480e29fe
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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