Trifluoroacetic acid → (S)-3-(6-Aminopyridin-3-yl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionic acid

HRID 2040009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040009
C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:24][C:25]([NH:27][C@@H:28]2[CH2:43][C:42]3=[CH:44][CH:45]=[C:39]([CH:40]=[CH:41]3)[O:38][CH2:37][CH2:36][CH2:35][CH2:34][O:33][CH2:32][C@H:31]([CH:46]([CH3:48])[CH3:47])[NH:30][C:29]2=[O:49])=[O:26])[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:24][C:25]([NH:27][C@@H:28]2[CH2:43][C:42]3=[CH:41][CH:40]=[C:39]([CH:45]=[CH:44]3)[O:38][CH2:37][CH2:36][CH2:35][CH2:34][O:33][CH2:32][C@H:31]([CH:46]([CH3:47])[CH3:48])[NH:30][C:29]2=[O:49])=[O:26])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67320386tert-butyl(S)-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionate

Produkt 1

HCID 44544625(S)-3-(6-Aminopyridin-3-yl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

160 mg (0.23 mmol) of tert-butyl (S)-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionate were dissolved in 6 ml of dichloromethane and, after addition of the same volume of TFA, stirred at RT. After 5 h, the mixture was concentrated and purified by preparative HPLC. The required fractions were combined, freed of acetonitrile, mixed with 1N hydrochloric acid, concentrated further and finally freeze dried. 108 mg of the title compound were obtained as hydrochloride.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. custompurified by preparative HPLC
  3. additionmixed with 1N hydrochloric acid
  4. concentrationconcentrated further
  5. customfinally freeze dried

Quellen und Nachweise

ORD-Eintrag
ord-0306183a3a7148518a07bcc629fe4531
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580777B2

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