Methyl acetopyruvate → HCID 59843200, Verbindung

HRID 2196552

Reaktionsgleichung

Reaktionsgleichung von HRID 2196552
O=[C:2]([CH2:7][C:8](=[O:10])[CH3:9])[C:3]([O:5][CH3:6])=[O:4].C[O-].[Na+].Br[C:15](=[N:20][NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:24][CH2:23]1)[C:16]([F:19])([F:18])[F:17].C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[C:8]([C:7]1[C:15]([C:16]([F:19])([F:18])[F:17])=[N:20][N:21]([CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:29])[CH2:26][CH2:27]2)[C:2]=1[C:3]([O:5][CH3:6])=[O:4])(=[O:10])[CH3:9]

Komponenten

7

Edukt 4

HCID 88600Methyl acetopyruvateHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 72576664Benzyl 4-(2-(1-bromo-2,2,2-trifluoroethylidene)hydrazinyl)piperidine-1-carboxylate

Produkt 1

HCID 59843200HCID 59843200, VerbindungAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of Methyl 2,4-dioxopentanoate (892 mg, 6.19 mmol) in MeOH (11.5 mL) at room temperature was added Sodium methoxide (25% in MeOH, 0.891 mL, 4.13 mmol). Then a solution of 111 (842 mg, 2.063 mmol) in MeOH (2.3 mL) was added drop-wise and the suspension was stirred for 10 min at room temperature, then for 2 h at 65° C. After cooling, the mixture was taken to dryness and AcOEt and saturated NaHCO3 were added, the organic layer was separated, dried over MgSO4, filtrated and evaporated and the residue was purified via Biotage (10% to 40% EtOAc/Hexane; 25S column) to afford 112 (361 mg, 38.6% yield) as red oil. LRMS (ESI): calc. 453.4; found 454.2 (MH)+.

Aufarbeitung

  1. waitfor 2 h at 65° C
  2. temperatureAfter cooling
  3. additionwere added
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. customevaporated
  8. customthe residue was purified via Biotage (10% to 40% EtOAc/Hexane; 25S column)

Quellen und Nachweise

ORD-Eintrag
ord-77022f1346174c788530c12e9d0ac4d5
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338437B2

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