3-Methylthiopropionate → 6-(2-Chlorophenyl)-6-(3-(methylthio)propanoyl)amino-2-cyclohexen-1-one

HRID 1769992Notes

Reaction equation

HRID 1769992 reaction equation
[NH2:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:7](=[O:8])[CH:6]=[CH:5][CH2:4][CH2:3]1.[CH3:16][S:17][CH2:18][CH2:19][C:20](O)=[O:21].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:2]1([NH:1][C:20](=[O:21])[CH2:19][CH2:18][S:17][CH3:16])[C:7](=[O:8])[CH:6]=[CH:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 5633-MethylthiopropionateHCID 162835DehydronorketamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 98836966-(2-Chlorophenyl)-6-(3-(methylthio)propanoyl)amino-2-cyclohexen-1-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (50 mg, 0.23 mmol), 3(methylthio)propanoic acid (prepared by the known base hydrolysis from the commercial methyl ester)(33 mg, 0.28 mmol), hydroxybenzotriazole (31 mg, 0.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.35 mmol) in dimethylformamide (1 ml) was stirred at room temperature for 18 h. The reaction was partitioned between saturated bicarbonate and ethyl acetate, the organic phase was washed with brine, dried (Na2SO4), and the solvent removed by evaporation. Purification was achieved by preparative thin layer chromatography on silica gel eluting with 1:1 ethyl acetate/hexane. Isolation of the UV active band at Rf 0.4 gave 6-(2-chlorophenyl)-6-(3-(methylthio)propanoyl)amino-2-cyclohexen- 1-one (60.6 mg, 65%). The title compound was found to be active at 6μm in the CMK assay.

Workup

  1. customThe reaction was partitioned between saturated bicarbonate and ethyl acetate
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed by evaporation
  5. customPurification

Sources & evidence

ORD record
ord-cb8836e5653742caa26b550d35d68061
Source dataset
uspto-grants-1995_01
Patent number
US05384331

Reaction notes

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