(2R)-2-aminopentan-1-ol → HCID 86618495, Verbindung

HRID 1436373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436373
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[N:6]=1.[NH2:14][C@H:15]([CH2:18][CH2:19][CH3:20])[CH2:16][OH:17]>C(Cl)Cl>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([NH:14][C@H:15]([CH2:18][CH2:19][CH3:20])[CH2:16][OH:17])[S:3][CH:4]=2)=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 5324727(2R)-2-aminopentan-1-olHCID 685381612-Bromo-4-(4-bromo-phenyl)-thiazole

Produkt 1

HCID 86618495HCID 86618495, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-bromo-4-(4-bromophenyl)-1,3-thiazole (2.9 g, 9.09 mmol), prepared in step 2 of Example 1, and (R)-(−)-2-amino-pentanol (2.82 g, 27.2 mmol) was stirred under nitrogen at 150° C. for 18 h. After cooling to room temperature, the residue was taken up in methylene chloride, applied to a Biotage FLASH 40+™ cartridge and the methylene chloride allowed to evaporate. Purification of the residue on the samplet on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge) using a linear gradient of 5% ethyl acetate-hexane to 100% ethyl acetate gave (2R)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}pentan-1-ol (2.56 g, 83%) as a yellow solid, mp 63-65° C.; MS (ESI) m/z 341 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customto evaporate
  3. customPurification of the residue on the samplet on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge)

Quellen und Nachweise

ORD-Eintrag
ord-304cb47d5bd149a29c9f2feafff8d50c
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618990B2

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