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

HRID 603248

반응식

HRID 603248 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71bb2a4bc7e54ee7b5d2025d10f96c61
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906645B2

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