Dimethylformamide → 6-(2-Aminoacetyl)amino-6-(2-chlorophenyl)-2-cyclohexen-1-one

HRID 1655671Notes

Reaction equation

HRID 1655671 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.C(OC(N[CH2:24][C:25]([OH:27])=[O:26])=O)(C)(C)C.[OH:28][C:29]1[C:37]2[N:36]=NN[C:33]=2[CH:32]=[CH:31][CH:30]=1.Cl.CN(C)CCCN=C=NCC.CN(C)C=[O:53]>>[CH:29]1[CH:37]=[C:33]2[C:7]([C:25]([OH:26])([OH:27])[C:24](=[O:53])[C:32]2=[CH:31][CH:30]=1)=[O:8].[NH2:36][CH2:37][C:29]([NH: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)=[O:28]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 162835DehydronorketamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 2

HCID 10236NinhydrinHCID 152252016-(2-Aminoacetyl)amino-6-(2-chlorophenyl)-2-cyclohexen-1-oneYield 43%

Procedure

A solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (50 mg, 0.23 mmol), N-(tert-butoxycarbonyl)glycine (47 mg, 0.27 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. The residue was dissolved in dichloromethane (2 ml), trifluoroacetic acid (2 ml) was added and stirred at room temperature for 1 h, followed by evaporation of the solvent and a normal work up. Purification was achieved by preparative thin layer chromatography on silica gel eluting with ethyl acetate. Isolation of the UV and ninhydrin positive band at Rf 0.2 gave 6-(2-aminoacetyl)amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (28 mg, 43%). The title compound was found to be active at 6 μm in both the CMK and DAMI 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. dissolutionThe residue was dissolved in dichloromethane (2 ml)
  6. additiontrifluoroacetic acid (2 ml) was added
  7. customfollowed by evaporation of the solvent
  8. customPurification

Sources & evidence

ORD record
ord-1af4e11118004765904be66249d73b0c
Source dataset
uspto-grants-1993_10
Patent number
US05250732

Reaction notes

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