Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

HRID 643835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643835
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:11]([C:12](=[O:26])N[C@]2(C(OC(C)(C)C)=O)C[C@H]2C=C)[CH2:10][CH:9]([O:27]C2C3C(=CC(OC)=CC=3)N=C(C3C=CC=CC=3)C=2)[CH:8]=1)=[O:6].Cl>CO>[O:26]=[C:12]1[CH:11]2[CH2:10][CH:9]([CH2:8][CH:7]2[C:5]([OH:4])=[O:6])[O:27]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 592041875-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester

Produkt 1

HCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acidAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of 30 (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) to give the title compound (2.51 g, 88%) as a yellow oil.

Aufarbeitung

  1. customevaporated
  2. additionPyridine (75 mL) and Ac2O (53 mL) were added
  3. waitto shake overnight at room temperature
  4. custompurified by flash column chromatography (ethyl acetate+1% acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-857a6a3b613749dab517a62fd97aa7e8
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700552B2

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