Sodium Hydroxide → Mk-8245

HRID 561212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561212
[Br:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]([O:24]CC)=[O:23])[N:20]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]([OH:24])=[O:23])[N:20]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 53388532Ethyl (5-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]isoxazol-5-yl}-2H-tetrazol-2-yl)acetate

Produkt 1

HCID 24988881Mk-8245

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl (5-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]isoxazol-5-yl}-2H-tetrazol-2-yl)acetate (1.3 g, 2.62 mmol) in THF (15 mL) and MeOH (5 mL) was added 1M sodium hydroxide (5.25 mL, 5.25 mmol). The mixture was stirred at room temperature for 1 h. Volatile solvents were removed in vacuo. The residue was diluted with water (20 mL), acidified with 1M HCl (6 mL) and extracted with EtOAc. The EtOAc extract was washed with water, dried (Na2SO4) and concentrated. The residue was triturated with diethyl ether to give the crude product, containing about 5% of the 1-isomer. Further purification by trituration in isopropyl acetate (2×, 80° C. overnight, then room temperature overnight) provided the title compound as a beige powder.

Aufarbeitung

  1. customVolatile solvents were removed in vacuo
  2. additionThe residue was diluted with water (20 mL)
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether
  9. customto give the crude product
  10. customFurther purification by trituration in isopropyl acetate (2×, 80° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-c0732cf615164cf896a991687af1f34e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063224B2

Notizen zur Reaktion

Wird geladen…