Triacetoxyperiodinane → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

HRID 1892056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1892056
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]1([CH:22]=[O:23])[CH2:21][CH2:20][CH2:19]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2]

Komponenten

5

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595653282-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

Produkt 1

HCID 595654712-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide (310 mg) in CH2Cl2 (30 ml) was added solid Dess Martin periodinane (480 mg) at room temperature, under nitrogen atmosphere. The mixture was stirred at the same temperature during 1 hour, then poured into sat aq NaHCO3 and extracted with CH2Cl2 (2×15 ml). The organic phase was separated and washed with aq Na2S2O3 and sat. aq. NaCl then dried over anhydrous sodium sulphate, filtered and evaporated under vacuum. The crude compound (250 mg) as yellow oil, was used for the next step without purification.

Aufarbeitung

  1. additionpoured
  2. extractionextracted with CH2Cl2 (2×15 ml)
  3. customThe organic phase was separated
  4. washwashed with aq Na2S2O3 and sat. aq. NaCl
  5. dry with materialthen dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe crude compound (250 mg) as yellow oil, was used for the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-c00f19984438428d9134a96813e2bf23
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507509B2

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