Methanol → 4'-[4-Cyclopropyl-2-ethoxy-5-(hydroxyiminomethyl)imidazol-1-ylmethyl]-3'-fluorobiphenyl-2-carboxylic acid t-butyl ester

HRID 1517744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517744
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=O)=[C:24]([CH:28]4[CH2:30][CH2:29]4)[N:23]=[C:22]3[O:31][CH2:32][CH3:33])=[C:16]([F:34])[CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:36][OH:37].N1C=CC=CC=1.CO>>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=[N:36][OH:37])=[C:24]([CH:28]4[CH2:29][CH2:30]4)[N:23]=[C:22]3[O:31][CH2:32][CH3:33])=[C:16]([F:34])[CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

5

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochloride2×HCID 592839094'-(4-Cyclopropyl-2-ethoxy-5-formylimidazol-1-ylmethyl)-3'-fluoro-biphenyl-2-carboxylic acid t-butyl ester

Produkt 1

HCID 722457754'-[4-Cyclopropyl-2-ethoxy-5-(hydroxyiminomethyl)imidazol-1-ylmethyl]-3'-fluorobiphenyl-2-carboxylic acid t-butyl esterAusbeute 80,2 %

Versuchsvorschrift

Compound A (1.21 g, 2.60 mmol), hydroxylamine hydrochloride (181 mg, 2.6 mmol), pyridine (10 mL, 100 mmol), and MeOH (10 mL, 300 mmol) were combined and stirred at room temperature overnight. Additional hydroxylamine hydrochloride (20 mg) was added and the mixture evaporated to dryness. The solids were dissolved in DCM (50 mL), washed with water (2×20 mL) and saturated aqueous NaCl (10 mL), dried over Na2SO4, and evaporated to dryness to afford compound B as a white solid (1.0 g).

Aufarbeitung

  1. customthe mixture evaporated to dryness
  2. dissolutionThe solids were dissolved in DCM (50 mL)
  3. washwashed with water (2×20 mL) and saturated aqueous NaCl (10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-61cf358675a342cca1f13a885ac2ddbe
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232306B2

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