2-Bromoethanol → 3-{(2s,4s)-1-Tert-butoxycarbonyl-4-[n (4-cyanophenylmethyl)-n-(2-hydroxyethyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

HRID 1791904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791904
Cl.Cl.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C@@H:13]2[CH2:17][NH:16][C@H:15]([C:18]([N:20]3[CH2:24][CH2:23][S:22][CH2:21]3)=[O:19])[CH2:14]2)=[CH:7][CH:6]=1)#[N:4].Br[CH2:26][CH2:27][OH:28].C(N([CH:35]([CH3:37])[CH3:36])CC)(C)C.[C:38](=[O:41])([O-])[OH:39].[Na+].[CH3:43]N1CCCC1=O>>[C:35]([O:39][C:38]([N:16]1[CH2:17][C@@H:13]([N:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)[CH2:26][CH2:27][OH:28])[CH2:14][C@H:15]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:41])([CH3:36])([CH3:37])[CH3:43]

Komponenten

6

Edukt 5

HCID 108982-BromoethanolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67507812HCID 67507812, Verbindung

Produkt 1

HCID 675081263-{(2s,4s)-1-Tert-butoxycarbonyl-4-[n (4-cyanophenylmethyl)-n-(2-hydroxyethyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The product (1.67 g) of Example 63 (1) was dissolved in N-methyl-2-pyrrolidone (12 mL), and 2-bromoethanol (1.42 mL) and diisopropylethylamine (2.09 mL) were added thereto. The mixture was stirred at 80° C. for 2 days. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-(2-hydroxyethyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (0.480 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf76bdab7fe6409e9a5ea4cc18b9883f
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074794B2

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