Pyridine → Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate

HRID 1842966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842966
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[CH2:9][OH:10])=[C:4]([F:14])[CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>CC(C)=O>[OH:12][CH2:11][C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:3][C:4]=1[F:14])([CH3:13])[CH2:9][OH:10]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721622-(4-Amino-2-fluorophenyl)-2-methylpropane-1,3-diol

Produkt 1

HCID 86672163Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-amino-2-fluorophenyl)-2-methylpropane-1,3-diol (1.5 g, 7.53 mmol, 1.0 eq) in acetone (50 mL) was added pyridine (1.2 g, 15.18 mmol, 2.0 eq) and phenyl chloroformate (1.3 g, 8.28 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 1 h. The acetone was evaporated, and the resulting residue was diluted with EtOAc (50 mL), washed with water (100 mL), brine (20 mL) and the solvent evaporated. The crude product was purified by silica CC using EtOAc/PE (3:2) as eluent to get phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate (1.7 g, 71%) as a white solid (TLC system: EtOAc/PE (7:3), Rf: 0.55).

Aufarbeitung

  1. customThe acetone was evaporated
  2. additionthe resulting residue was diluted with EtOAc (50 mL)
  3. washwashed with water (100 mL), brine (20 mL)
  4. customthe solvent evaporated
  5. customThe crude product was purified by silica CC

Quellen und Nachweise

ORD-Eintrag
ord-955180924293465d9de3ba230f61d19d
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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