2-Bromoethanol → HCID 67508126, Verbindung

HRID 1829112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829112
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+].[CH2:43](N1CCCC1=O)C>>[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 17595N-ethyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67507812HCID 67507812, Verbindung

Produkt 1

HCID 67508126HCID 67508126, Verbindung

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The product (1.67 g) of Example 63 (1) was dissolved in N-ethyl-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-413d0b71a5ac4662815e44d57da3a1b7
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060722B2

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