Water → (1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide

HRID 454964ノート

反応式

HRID 454964 の反応式
[C:1]1([C@H:7]2[CH2:9][C@@H:8]2[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH2:23])[CH2:21][CH3:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>ClCCl.CN(C)C=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C@@H:20]([NH:23][C:10]([C@H:8]2[CH2:9][C@@H:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:12])[CH2:21][CH3:22])=[CH:18][CH:19]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 7785172-Phenyl-1-cyclopropanecarboxylic acid, (1S-trans)-HCID 7127717(S)-1-(4-bromophenyl)propan-1-amine

生成物 1

HCID 67432459(1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide収率 92.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (1S,2S)-2-phenyl-cyclopropanecarboxylic acid (170 mg, 1.05 mmol) in dichloromethane (10 ml) was added oxallyl dichloride (145 mg, 1.2 mmol) followed by a few drops of N,N-dimethylformamide at RT. The reaction mixture was stirred at RT for 45 mins before it was concentrated down and dissolved in dichloromethane (1.5 ml). The solution was added slowly to a solution of (S)-1-(4-bromo-phenyl)-propylamine (250 mg, 1.0 mmol, HCl salt) and triethylamine (222 mg, 2.2 mmol) in dichloromethane (10 ml) at 0° C. The resulting reaction mixture was stirred at RT for 1.5 h. Water was added and the aqueous layer was extracted by dichloromethane. Organic layer was dried by magnesium sulfate and concentrated. The residue was purified via column chromatography on silica gel to afford (1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide (330 mg, 92%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.37 (d, J=8.6 Hz, 2H), 7.15-7.23 (m, 2H), 7.11 (d, J=7.3 Hz, 1H), 7.08 (d, J=8.3 Hz, 2H), 6.98 (d, J=7.3 Hz, 2H), 5.75 (d, J=7.6 Hz, 1H), 4.77 (q, J=7.5 Hz, 1H), 2.31-2.41 (m, 1H), 1.65-1.81 (m, 2H), 1.48-1.59 (m, 2H), 1.12-1.23 (m, 1H), 0.82 (t, J=7.4 Hz, 3H); LRMS (ESI) (M+1)=360.04. Molecular Formula=C19H20BrNO.

後処理

  1. concentrationwas concentrated down
  2. dissolutiondissolved in dichloromethane (1.5 ml)
  3. customThe resulting reaction mixture
  4. stirringwas stirred at RT for 1.5 h
  5. extractionthe aqueous layer was extracted by dichloromethane
  6. dry with materialOrganic layer was dried by magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography on silica gel

出典と根拠

ORDレコード
ord-113f1d16fab24012a1c7329658d789c1
出典データセット
uspto-grants-2013_07
特許番号
US08497271B2

反応ノート

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