p-Toluenesulfonic acid → HCID 45256133, compound

HRID 1809428Notes

Reaction equation

HRID 1809428 reaction equation
[CH3:1][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18](=[O:31])[C:19]([CH3:30])([S:21]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)(=[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.C(O)C>[OH:4][CH2:3][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18](=[O:31])[C:19]([CH3:30])([S:21]([CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)(=[O:23])=[O:22])[CH3:20])[O:14][N:13]=1)([CH3:11])[CH3:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 45111496HCID 45111496, compound

Product 1

HCID 45256133HCID 45256133, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of 98 g (0.21 mol) of N-{3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide in DCM/ethanol (1/1, 1.2 L) is treated with 129 g (0.42 mol) 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 (0.5 L) and methanol (0.5 L) twice. The combined filtrates are concentrated under reduced pressure and the resulting tan residue is slurried in heptanes/ethyl acetate (7/3, 4×1 L) to yield 65 g of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)propionamide as a white powder. Yield 82%; ES-MS: m/z 375 [M+H], mp 191-192° C.

Workup

  1. customThe resin is removed by filtration
  2. washwashed
  3. concentrationThe combined filtrates are concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc342b6df76243318e8bc744f7e614c4
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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