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Methyl Glycolate → {5-[1-(4-Cyano-3-fluorophenyl)-1-hydroxyethyl]imidazol-1-yl}acetic acid methyl ester

HRID 2306217
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2306217
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)([OH:11])[CH3:10])=[CH:5][C:4]=1[F:36])#[N:2].[C:37]([O:41][CH3:42])(=[O:40])[CH2:38]O.C(N(CC)C(C)C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[CH3:42][O:41][C:37](=[O:40])[CH2:38][N:13]1[C:12]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:36])[CH:5]=2)([OH:11])[CH3:10])=[CH:16][N:15]=[CH:14]1
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Komponenten

6

Edukt 4

HCID 66774Methyl GlycolateHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 184336071-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

Produkt 1

HCID 53834038{5-[1-(4-Cyano-3-fluorophenyl)-1-hydroxyethyl]imidazol-1-yl}acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(4-cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol, as described above in Step C, (200 mg, 0.42 mmol), methyl glycolate (35 mg, 0.39 mmol), and N,N-diisopropylethylamine (65 mg, 0.51 mmol) in dry CH2Cl2 (10 mL), under argon, at −78° C., was added trifluoromethanesulfonic anhydride (110 mg, 0.39 mmol) dropwise. The mixture was allowed to warm slowly to ambient temperature, then the solvent was removed in vacuo. The residue was dissolved in MeOH (10 mL) and the solution was heated to reflux for 1 hour, then concentrated to dryness. The residue was purified by silica gel chromatography, eluting with 4% MeOH—0.4% NH4OH in CHCl3, to yield the titled product as a white solid.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. temperaturethe solution was heated
  4. temperatureto reflux for 1 hour
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 4% MeOH—0.4% NH4OH in CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-3235987975cd41b79c20e200728d3ab9
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06441017B1

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