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

HRID 2371204

Reaktionsgleichung

Reaktionsgleichung von HRID 2371204
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-11f7bf7c32e440058b5e82921d18cfea
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710224B2

Verknüpfte Notizen

Wird geladen…