Reaktion #738326

ord-a25e5628c0914b128ccbeb0ed800c2c6

Reaktionsgleichung

Cl.N[C@@H](Cc1ccc(F)cc1)C(=O)N1CCC(O)CC1
(S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride
O=C(O)c1cc2cc(F)ccc2[nH]1
5-fluoro-1H-indole-2-carboxylic acid
O=C(N[C@@H](Cc1ccc(F)cc1)C(=O)N1CCC(O)CC1)c1cc2cc(F)ccc2[nH]1
5-Fluoro-1H-indole-2-carboxylic acid [(1S)-(4-fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product was triturated once with 1:1 ether-hexanes and once with hexanes
  2. 2
    Filtrationthe resulting suspension filtered
  3. 3
    Sonstigethe collected solid dried
  4. 4
    SonstigeHPLC (60/40) 3.69 minutes (95%)

Vorschrift

(S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride (0.5 mmol) and 5-fluoro-1H-indole-2-carboxylic acid (0.5 mmol) were coupled according to Procedure A. The crude product was triturated once with 1:1 ether-hexanes and once with hexanes. The resulting solid was boiled in ethyl acetate, the resulting suspension filtered, and the collected solid dried. Yield 103 mg, 48%; HPLC (60/40) 3.69 minutes (95%); PBMS 428 (MH+, 100%);

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06277877B1uspto-grants-2001_08