Ethyl trifluoromethanesulphonate → HCID 58405789, Verbindung

HRID 44812

Reaktionsgleichung

Reaktionsgleichung von HRID 44812
[N:1]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH:2]1[C:14]([O:16][CH3:17])=[O:15].C[Si](C)(C)N[Si](C)(C)C.[K].FC(F)(F)S(O[CH2:44][CH3:45])(=O)=O>C1COCC1>[CH2:44]([C:2]1([C:14]([O:16][CH3:17])=[O:15])[CH2:3][N:4]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[CH2:5][CH2:6][N:1]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH3:45]

Komponenten

5

Edukt 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 44519651-Benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylateHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt

Produkt 1

HCID 58405789HCID 58405789, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Following the procedure according to WO 2005/079799 (the disclosure of which is hereby incorporated by reference with respect to this synthesis), 1-benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (II-JJ, 1.1 g, 2.9 mmol) was dissolved in 6 mL of dry THF and cooled to −78° C. Potassium hexamethyldisilazane (0.5M solution in toluene, Aldrich, 10 mL, 5.0 mmol) was added by syringe, and the reaction mixture stirred at −78° C. for 75 min. Ethyl trifluoromethanesulfonate (0.65 mL, 5.0 mmol) was added dropwise by syringe to this mixture, and then the reaction was allowed to warm to rt for 5 h. The reaction was quenched with saturated sodium bicarbonate solution, and the mixture was extracted twice with ethyl acetate. The combined organics were dried with MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (0-10% methanol/DCM gradient elution) gave 1-Benzyl 4-tert-butyl 2-methyl 2-ethylpiperazine-1,2,4-tricarboxylate (compound III-JJ) as a yellow oil, approximately 5:1 ratio of methyl and ethyl esters (1.06 g): LCMS: [M+Na]+=429.2 (60%); [M-Boc+H]+=307.1 (100%).

Aufarbeitung

  1. temperatureto warm to rt for 5 h
  2. customThe reaction was quenched with saturated sodium bicarbonate solution
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialThe combined organics were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washFlash chromatography (0-10% methanol/DCM gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-26c8aeccf99c4fbd8880b0098801f43b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541418B2

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