1,2-Dichloroethane → 4-Cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid cyclohexyl-methyl-amide

HRID 252463Notes

Reaction equation

HRID 252463 reaction equation
[C:1]([CH:3]([CH2:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]=1[N+:23]([O-:25])=[O:24])[CH2:4][CH2:5][C:6]([OH:8])=O)#[N:2].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl.[CH3:47][NH:48][CH:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>ClCCl>[CH:49]1([N:48]([CH3:47])[C:6](=[O:8])[CH2:5][CH2:4][CH:3]([C:1]#[N:2])[CH2:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=[CH:12][C:11]=2[N+:23]([O-:25])=[O:24])[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 574757204-Cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid

Product 1

HCID 672695344-Cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid cyclohexyl-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid (0.230 g, 0.68 mmol) was dissolved in dichloromethane (1.5 mL) followed by addition of HOBt (0.103 g, 0.68 mmol), triethylamine (0.170 mL, 0.68 mmol), EDC (0.194 g, 1.01 mmol) and N-methyl-cyclohexylamine (0.09 mL, 0.68 mmol). The reaction was allowed to proceed for 16 h after which time, the solvent was removed under reduced pressure. The resulting mixture was dissolved in ethyl acetate and washed 3 times with 10% sodium carbonate solution, one time with saturated brine solution, 3 times with 1N HCl and then again one time with brine wash. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield a residue. The residue was purified with flash chromatography using a mixture of 65:35 heptanes:ethyl acetate as the mobile phase to yield a residue.

Workup

  1. customafter which time, the solvent was removed under reduced pressure
  2. dissolutionThe resulting mixture was dissolved in ethyl acetate
  3. washwashed 3 times with 10% sodium carbonate solution, one time with saturated brine solution, 3 times with 1N HCl
  4. washagain one time with brine wash
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customto yield a residue
  8. customThe residue was purified with flash chromatography
  9. additiona mixture of 65:35 heptanes
  10. customethyl acetate as the mobile phase to yield a residue

Sources & evidence

ORD record
ord-426dc85434c24783a3ba03e323e1afcf
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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