Dehydronorketamine → 6-Biotinoylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one

HRID 1769993Notes

Reaction equation

HRID 1769993 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.[OH:16][C:17]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]1[C@@H:31]2[C@@H:26]([NH:27][C:28]([NH:30]2)=[O:29])[CH2:25][S:24]1)=O.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:17]([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:16])[CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]1[C@@H:31]2[C@@H:26]([NH:27][C:28]([NH:30]2)=[O:29])[CH2:25][S:24]1

Participants

5

Reactant 3

HCID 162835DehydronorketamineHCID 171548BiotinHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 542752296-Biotinoylamino-6-(2-chlorophenyl)-2-cyclohexen-1-oneYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (50 mg, 0.23 mmol), (+)-biotin (56 mg, 0.23 mmol), hydroxybenzotdazole (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 42 h. The reaction was partitioned between water and ethyl acetate, the organic phase was washed with water, brine, dried (Na2SO4), and the solvent removed by evaporation. Flash chromatography on silica gel eluted with 17:3 ethyl acetate / hexane afforded 6-biotinoylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one (32.7 mg, 32%).

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washthe organic phase was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed by evaporation
  5. washFlash chromatography on silica gel eluted with 17:3 ethyl acetate / hexane

Sources & evidence

ORD record
ord-b06ef4ef8a224f03bcb0d2078caa1ce1
Source dataset
uspto-grants-1995_01
Patent number
US05384331

Reaction notes

Loading…