Water → 5-(Benzo[1,3]dioxol-5-ylmethyl-tert-butoxycarbonyl-amino)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pentanoic acid ethyl ester

HRID 1170487

Reaktionsgleichung

Reaktionsgleichung von HRID 1170487
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[S:10][N:9]=[C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[N:7]=1)[CH3:2].[H-].[Na+].[C:19]([O:23][C:24](=[O:40])[N:25]([CH2:30][C:31]1[CH:39]=[CH:38][C:34]2[O:35][CH2:36][O:37][C:33]=2[CH:32]=1)[CH2:26][CH2:27][CH2:28]Br)([CH3:22])([CH3:21])[CH3:20].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:6]1[S:10][N:9]=[C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[N:7]=1)[CH2:28][CH2:27][CH2:26][N:25]([CH2:30][C:31]1[CH:39]=[CH:38][C:34]2[O:35][CH2:36][O:37][C:33]=2[CH:32]=1)[C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:40])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 58654358(3-Imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-acetic acid ethyl esterHCID 59551900Benzo[1,3]dioxol-5-ylmethyl-(3-bromo-propyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 686951045-(Benzo[1,3]dioxol-5-ylmethyl-tert-butoxycarbonyl-amino)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pentanoic acid ethyl esterAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-acetic acid ethyl ester (240 mg, 1.0 mmol) in DMSO (2 mL) was added NaH (70 mg of a 60% dispersion on mineral oil, 1.8 mmol) and benzo[1,3]dioxol-5-ylmethyl-(3-bromo-propyl)-carbamic acid tert-butyl ester (370 mg, 1.0 mmol) subsequently. The solution was stirred for 2 h at 60° C. Water (4 mL) was added and the solution was extracted with ethyl acetate, washed with brine and dried over Na2SO4. Evaporation of the solvent gave a residue which was purified by column chromatography to afford 370 mg (70%) of 5-(benzo[1,3]dioxol-5-ylmethyl-tert-butoxycarbonyl-amino)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pentanoic acid ethyl ester as a red oil.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave a residue which
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a34e5a27fb024b6cbf3fef4cd6bde1d5
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825256B2

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