Potassium Carbonate → 4-[4-(Diethoxy-phosphorylmethyl)-piperazin-1-ylmethyl]-benzoic acid

HRID 48936ノート

反応式

HRID 48936 の反応式
[N:1]1([CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:17]([O:19][P:20]([CH2:25]Cl)(=[O:24])[O:21][CH2:22][CH3:23])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C.[Cl-].[Na+].O>[CH2:17]([O:19][P:20]([CH2:25][N:4]1[CH2:5][CH2:6][N:1]([CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:2][CH2:3]1)([O:21][CH2:22][CH3:23])=[O:24])[CH3:18]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 76633Phosphonic acid, P-(chloromethyl)-, diethyl esterHCID 176060554-(1-Piperazinylmethyl)benzoic acid

生成物 1

HCID 206345494-[4-(Diethoxy-phosphorylmethyl)-piperazin-1-ylmethyl]-benzoic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 4-Piperazin-1-ylmethyl-benzoic acid (4c) and chloromethyl-phosphonic acid diethyl ester (4d) in ethanol was added potassium carbonate. The resulting reaction mixture was refluxed, then cooled to room temperature, diluted with brine, acidified to pH˜4, and extracted with EtOAc until the aqueous layer showed little or no evidence of product by HPLC. The combined organics were dried over MgSO4 and concentrated on rotary evaporator. The desired product was purified by silica gel flash chromatography.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed
  3. extractionextracted with EtOAc until the aqueous layer
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated on rotary evaporator
  6. customThe desired product was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-ed6d76fa55dd42c390a02af3e2ddcee4
出典データセット
uspto-grants-2004_03
特許番号
US06706699B2

反応ノート

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