Potassium Hydroxide → 5-(benzyloxy)-4-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)benzoic acid

HRID 1022484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022484
[CH2:1]([O:8][C:9]1[C:10]([F:27])=[CH:11][C:12]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:13]([CH:19]=1)[C:14]([O:16]CC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)(C)C.O>[CH2:1]([O:8][C:9]1[C:10]([F:27])=[CH:11][C:12]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:13]([CH:19]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 67495078ethyl 5-(benzyloxy)-4-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)benzoate

Produkt 1

HCID 667327195-(benzyloxy)-4-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)benzoic acidAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g of the compound obtained in Step 4.3 and 0.45 g of KOH in 16 ml of isopropanol and 4 ml of water is irradiated in a microwave field for 20 minutes at 130° C. The reaction medium is evaporated under reduced pressure. Water is added, the resulting mixture is acidified with aqueous 1N HCl solution to pH 3 and this mixture is extracted with EtOAc. The organic phase is dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure to give 0.91 g of the expected product.

Aufarbeitung

  1. customis irradiated in a microwave field for 20 minutes at 130° C
  2. customThe reaction medium is evaporated under reduced pressure
  3. additionWater is added
  4. extractionthis mixture is extracted with EtOAc
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-47b0961239a242378467d8eac3416d51
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722659B2

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