Triacetoxyperiodinane → (3-Ethynyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide

HRID 1962861

Reaktionsgleichung

Reaktionsgleichung von HRID 1962861
[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:25][CH3:26])[C:15]([NH:17][C:18]([CH2:22][O:23][CH3:24])([CH3:21])[CH2:19][OH:20])=[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:25][CH3:26])[C:15]([NH:17][C:18]([CH2:22][O:23][CH3:24])([CH3:21])[CH:19]=[O:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2]

Komponenten

5

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595653712-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

Produkt 1

HCID 59565278(3-Ethynyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamideAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (200 mg) in dry CH2Cl2 (15 ml) was treated with Dess-Martin periodinane (295 mg). The mixture was stirred at room temperature during 1 h then poured on sat aq NaHCO3. After separation the water phase was washed twice with CH2Cl2 The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated. The crude residue was purified by column chromatography (cyclohexane/ethyl acetate 1:1) to give (3-Ethynyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide (120 mg) as yellowish oil as a mixture of diastereoisomers.

Aufarbeitung

  1. additionthen poured
  2. customAfter separation the water phase
  3. washwas washed twice with CH2Cl2 The combined organic phases
  4. washwere washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (cyclohexane/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d725e15165c049f390a39b5233ffff83
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415272B2

Verknüpfte Notizen

Wird geladen…