Ethyl Acetate → N-Cyclohexyl-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)-N-(2-oxoethyl)propanamide

HRID 909883Notes

Reaction equation

HRID 909883 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.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 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)propanamideYield 107.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide (0.5 g) was stirred in DCM (10 mL) followed by the addition of p-toluenesulfonic acid monohydrate (0.43 g). The mixture was stirred for 1 h. Ethyl acetate was added followed by sodium hydrogen carbonate solution. The aqueous phase was removed and the remaining organic phase washed once with water, once with brine, dried over sodium sulphate, filtered and the solvent removed to afford the desired material as an oil (0.48 g). This material was used in the next step directly. MS [M+H]+=398 (MultiMode+)

Workup

  1. customThe aqueous phase was removed
  2. washthe remaining organic phase washed once with water, once with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-549cec2ee57042758ba947d5c7b7cc7a
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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