p-Toluenesulfonic acid monohydrate → N-Cyclohexyl-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)-N-(2-oxoethyl)propanamide

HRID 909887Notes

Reaction equation

HRID 909887 reaction equation
[CH:1]1([N:7]([CH2:27][CH:28](OC)[O:29]C)[C:8](=[O:26])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[CH:1]1([N:7]([CH2:27][CH:28]=[O:29])[C:8](=[O:26])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59290438N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Product 1

HCID 44553042N-Cyclohexyl-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)-N-(2-oxoethyl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide (50.3 g) in tetrahydrofuran (150.9 mL) was added to a solution of p-toluenesulfonic acid monohydrate (86.3 g) in tetrahydrofuran (100.1 mL) at 20° C. to give a solution. A line wash of tetrahydrofuran (50.3 mL) was then added and the solution stirred at ambient temperature for 1 h before being added to a solution of sodium hydroxide (19.6 g) and sodium chloride (100.6 g) in water (502.9 mL) at 5° C. A line wash of tetrahydrofuran (25.1 mL) was then added and the solution warmed to 20° C. 1-Butanol (100.6 mL) was added and the layers separated. The separated organic layer can be evaporated to dryness to afford the sub-titled compound as an orange/brown oil or the solution used directly in the next Step. MS [M+H]+=398.2 (MultiMode+)

Workup

  1. customto give a solution
  2. washA line wash of tetrahydrofuran (50.3 mL)
  3. additionwas then added
  4. additionbefore being added to a solution of sodium hydroxide (19.6 g) and sodium chloride (100.6 g) in water (502.9 mL) at 5° C
  5. washA line wash of tetrahydrofuran (25.1 mL)
  6. additionwas then added
  7. temperaturethe solution warmed to 20° C
  8. addition1-Butanol (100.6 mL) was added
  9. customthe layers separated
  10. customThe separated organic layer can be evaporated to dryness

Sources & evidence

ORD record
ord-2018283eff5643f4bf9d1f2098f25f3b
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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