Ethyl Acetate → HCID 12016496, Verbindung

HRID 1264616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264616
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:28]([O-])=O)=[C:6]([CH:27]=1)[CH2:7][N:8]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11].O.O.[Sn](Cl)(Cl)(Cl)Cl.[C:38]([O-])(O)=O.[Na+].C(O[CH2:47][CH3:48])(=O)C>C(O)C>[NH2:28][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:27][C:6]=1[CH2:7][N:8]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:38]#[C:47][CH3:48])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18612902HCID 18612902, VerbindungHCID 85782573Tin tetrachloride dihydrate

Produkt 1

HCID 12016496HCID 12016496, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Methyl 2-{(5-fluoro-2-nitrobenzyl)[(4-methoxyphenyl)sulfonyl]amino}-3-hydroxypropanoate (1.0 g, 2.08 mmol) was dissolved in ethanol (18 mL). To this was added tin chloride dihydrate (2.35 g, 10.4 mmol) and the reaction was heated to 70° C. for 2 hours. The reaction was then cooled to room temperature and ice water followed by NaHCO3 was added to bring the solution to pH 8. Ethyl acetate was added and the suspension was filtered through celite. The organic layer was separated and washed with brine, dried over Na2SO4 concentrated in vacuo and chromatographed using 1:1 hexane:ethyl acetate as eluant to provide 0.55 g (58%) of the desired product as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. additionwas added
  3. filtrationthe suspension was filtered through celite
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-c775419fbf1d4407a48e9b8f18c7a213
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544984B1

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