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

HRID 502887ノート

反応式

HRID 502887 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f6a3ca3ee3814becb52e2ccaefeb81f5
出典データセット
uspto-grants-2010_08
特許番号
US07776882B2

反応ノート

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