Hydrochloric Acid → 2-(3-Fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid

HRID 62911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62911
[Li+].[OH-].OO.C([C@@H]1COC(=O)N1[C:18]([CH:20]1[CH2:22][CH:21]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([F:31])[CH:24]=1)=[O:19])C1C=CC=CC=1.[O-:32]S([O-])=O.[Na+].[Na+].Cl>O.C1COCC1.O>[F:31][C:25]1[CH:24]=[C:23]([CH:21]2[CH2:22][CH:20]2[C:18]([OH:19])=[O:32])[CH:28]=[CH:27][C:26]=1[O:29][CH3:30]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 90118203(R)-4-benzyl-3-[2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

Produkt 1

HCID 211905602-(3-Fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

After LiOH (0.059 g, 1.40 mmol) was dissolved in water (5 mL), H2O2 (0.3 mL, 3.52 mmol) was added thereto, and the mixture was stirred at room temperature for 30 minutes. The reactant was added to the solution of (R)-4-benzyl-3-[2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-o n (0.325 g, 0.88 mmol) obtained in Step C of Preparation Example 62 in THF/H2O (17 mL/4.4 mL) at 0° C., and the mixture was stirred for 1 hour. After the termination of the reaction, Na2SO3 (1 g) dissolved in water (5 mL) was added thereto, and the mixture was stirred at 0° C. for 1 hour. 6N HCl was added thereto to adjust the pH to 2, and the reactant was extracted with ethyl acetate. The organic layer was separated, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound, which was used in the next step without a separate purification process

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. additionwas added
  3. stirringthe mixture was stirred at 0° C. for 1 hour
  4. extractionthe reactant was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ffcb7a33d12c4b8daf6134e6956047d3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447044B2

Notizen zur Reaktion

Wird geladen…