Pyridine → Phenyl 3-fluoro-4-(3-hydroxyoxetan-3-yl)phenylcarbamate

HRID 1842919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842919
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:12])[CH2:11][O:10][CH2:9]2)=[C:4]([F:13])[CH:3]=1.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>CC(C)=O>[F:13][C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][C:5]=1[C:8]1([OH:12])[CH2:9][O:10][CH2:11]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721503-(4-Amino-2-fluorophenyl)oxetan-3-ol

Produkt 1

HCID 86672149Phenyl 3-fluoro-4-(3-hydroxyoxetan-3-yl)phenylcarbamateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(4-amino-2-fluorophenyl)oxetan-3-ol (0.93 g, 5.08 mmol, 1.0 eq) in acetone (10 mL) was added pyridine (0.82 mL, 10.16 mmol, 2.0 eq) and phenyl chloroformate (0.7 mL, 5.59 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 1 h. The solvents was evaporated and the crude product was extracted with EtOAC (25 mL), diluted with water (15 mL), washed with brine (10 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. The resulting residue was washed with diethyl ether (25 mL) to get phenyl 3-fluoro-4-(3-hydroxyoxetan-3-yl)phenylcarbamate (0.892 g, 59%) as a off white solid (TLC system: 100% EtOAc, Rf: 0.55).

Aufarbeitung

  1. customThe solvents was evaporated
  2. extractionthe crude product was extracted with EtOAC (25 mL)
  3. additiondiluted with water (15 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. washThe resulting residue was washed with diethyl ether (25 mL)

Quellen und Nachweise

ORD-Eintrag
ord-e5e2127bc1e2447b98a6caef591f6ae8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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