Sodium Bicarbonate → N-(3,4-Dichlorophenyl)-4-{[(2R)-4-tert-butoxycarbonylpiperazin-2-yl]carbonyl}piperazine-1-carboxamide

HRID 603248

反応式

HRID 603248 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]1C(O)=O)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:67](=O)(O)[O-:68].[Na+]>CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:67]([C@H:27]3[CH2:26][N:25]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:30][CH2:29][NH:28]3)=[O:68])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamideHCID 24820285(2R)-1-(tert-Butoxycarbonyl)piperazine-2-carboxylic acid

生成物 1

HCID 67220684N-(3,4-Dichlorophenyl)-4-{[(2R)-4-tert-butoxycarbonylpiperazin-2-yl]carbonyl}piperazine-1-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

N-(3,4-Dichlorophenyl)piperazine-1-carboxamide (596 mg) and (2R)-1-BOC-piperazine-2-carboxylic acid (500 mg) were dissolved in N,N-dimethylformamide (30 ml) and stirred at 0° C. Triethylamine (0.61 ml) was added followed by PYBOP reagent (1.13 g). The mixture was allowed to warm to room temperature overnight, poured into saturated aqueous sodium bicarbonate (60 ml) and extracted with ethyl acetate (2×100 ml), adding a little water during the process to dissolve precipitated sodium bicarbonate. The combined organic extracts were treated with brine (100 ml), dried (sodium sulphate), concentrated in vacuo and adsorbed onto silica for purification by chromatography eluting with 0-15% methanol dichloromethane. This gave the product as a white glass (710 mg).

後処理

  1. temperatureto warm to room temperature overnight
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. additionadding a little water during the process
  4. dissolutionto dissolve
  5. customprecipitated sodium bicarbonate
  6. additionThe combined organic extracts were treated with brine (100 ml)
  7. dry with materialdried (sodium sulphate)
  8. concentrationconcentrated in vacuo
  9. customadsorbed onto silica for purification by chromatography
  10. washeluting with 0-15% methanol dichloromethane

出典と根拠

ORDレコード
ord-71bb2a4bc7e54ee7b5d2025d10f96c61
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

関連ノート

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