Triethylamine → Methyl 2-(1-methyl-3-(N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetate

HRID 1192900ノート

反応式

HRID 1192900 の反応式
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16](NC(=O)OCCCl)(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:26]CN(CC)CC.[NH2:33][C:34]1([CH2:41][C:42]([O-:44])=[O:43])[CH2:39][CH2:38][CH2:37][N:36]([CH3:40])[CH2:35]1>CC#N>[CH3:40][N:36]1[CH2:37][CH2:38][CH2:39][C:34]([CH2:41][C:42]([O:44][CH3:26])=[O:43])([NH:33][S:16](=[O:17])(=[O:18])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=2)[CH2:35]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 581099762-chloroethyl N-(4-octylphenyl)sulfamoylcarbamateHCID 866498462-(3-Amino-1-methylpiperidin-3-yl)acetate

生成物 1

HCID 66864494Methyl 2-(1-methyl-3-(N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetate収率 27.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 2-chloroethyl N-(4-octylphenyl)sulfamoylcarbamate (156 mg, 0.4 mmol) in CH3CN (10 mL) was treated with Et3N (0.14 mL, 1 mmol) and refluxed for 25 min. and cooled. A solution of 2-(3-amino-1-methylpiperidin-3-yl)acetate (62 mg, 0.33 mmol) was added and the resulting mixture was refluxed for 4 h. After removal of the solvent in vacuo, the residue was dissolved in dichloromethane (40 mL) and washed with sat. NaHCO3 (10 mL), H2O (10 mL), brine (10 mL) and dried (Na2SO4). After evaporation, the residue was purified by flash chromatography (EtOAc/hex 1:4 to EtOAc) to give the title compound (41 mg, 27%) as colorless oil. MS ESI 454.3[M+H]+, calcd for [C23H39N3O4S+H]+ 454.27.

後処理

  1. temperaturerefluxed for 25 min.
  2. temperaturecooled
  3. temperaturethe resulting mixture was refluxed for 4 h
  4. customAfter removal of the solvent in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (40 mL)
  6. washwashed with sat. NaHCO3 (10 mL), H2O (10 mL), brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. customAfter evaporation
  9. customthe residue was purified by flash chromatography (EtOAc/hex 1:4 to EtOAc)

出典と根拠

ORDレコード
ord-fd1b85da27084615b130ce0d77af19db
出典データセット
uspto-grants-2014_03
特許番号
US08680282B2

反応ノート

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