4-Carboxymethoxy-3-methyl-benzoic Acid Methyl Ester → 4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-2-oxo-ethoxy}-3-methyl-benzoic Acid Methyl Ester

HRID 220848ノート

反応式

HRID 220848 の反応式
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([OH:14])=O)=[C:6]([CH3:15])[CH:5]=1.Cl.Cl.[CH3:19][C:20]([CH3:30])([CH3:29])[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C1C=CN=CC=1)C.ClCCl.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([N:26]2[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[CH3:19])[CH2:24][CH2:25]2)=[O:14])=[C:6]([CH3:15])[CH:5]=1

参加物

6

反応物 2

HCID 575553254-Carboxymethoxy-3-methyl-benzoic Acid Methyl EsterHCID 670538001-(3,3-Dimethyl-butyl)-piperazine dihydrochloride

生成物 1

HCID 670538104-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-2-oxo-ethoxy}-3-methyl-benzoic Acid Methyl Ester収率 55%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

WSCD (5.14 g, 27.2 mmol) and DMAP (1.64 g, 13.6 mmol) were added to a solution of 4-carboxymethoxy-3-methyl-benzoic acid methyl ester from Example E41.2 (3.04 g, 13.6 mmol) in dichloromethane (100 ml) and triethylamine (5 ml). The mixture was stirred for 1 h at room temperature then 1-(3,3-dimethyl-butyl)-piperazine dihydro-chloride from Example E4 (3.67 g, 14.9 mmol) was added. The mixture was stirred for 20 h at room temperature then solvents were removed in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (2.8 g, 55%).

後処理

  1. stirringThe mixture was stirred for 20 h at room temperature
  2. customsolvents were removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

出典と根拠

ORDレコード
ord-7f7f9a44bc214835adeb44cf36180ae2
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

反応ノート

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