1,1'-Carbonyldiimidazole → tert-Butyl (S)-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-2-[3-((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-11-yl)ureido]propionate

HRID 1023007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023007
[NH2:1][C@@H:2]1[CH2:16][C:15]2=[CH:17][N:12]([CH:13]=[N:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C@H:5]([CH:18]([CH3:20])[CH3:19])[NH:4][C:3]1=[O:21].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[NH2:34][C@@H:35]([CH2:43][C:44]1[CH:45]=[N:46][C:47]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[CH:48][CH:49]=1)[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CN(C=O)C>[C:54]([O:53][C:51]([NH:50][C:47]1[N:46]=[CH:45][C:44]([CH2:43][C@H:35]([NH:34][C:22]([NH:1][C@@H:2]2[CH2:16][C:15]3=[CH:17][N:12]([CH:13]=[N:14]3)[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C@H:5]([CH:18]([CH3:19])[CH3:20])[NH:4][C:3]2=[O:21])=[O:23])[C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[CH:49][CH:48]=1)=[O:52])([CH3:57])([CH3:56])[CH3:55]

Komponenten

5

Edukt 3

HCID 682631,1'-Carbonyldiimidazole2×HCID 58360487tert-Butyl (S)-2-amino-3-(6-tert-butoxycarbonylaminopyridin-3-yl)propionateHCID 67028858(8S,11R)-11-Amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-one

Produkt 1

HCID 86655970tert-Butyl (S)-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-2-[3-((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-11-yl)ureido]propionateAusbeute 21.603.088 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 56 mg (190 pmol) of (8S,11R)-11-amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-one from step D in 5 ml of DMF was cooled to 0° C. and, while stirring, 32 mg (194 μmol) of 1,1′-carbonyldiimidazole were added. The mixture was stirred for 30 min, and then 64 mg (190 pmol) of tert-butyl(S)-2-amino-3-(6-tert-butoxycarbonylaminopyridin-3-yl)propionate were added, and the mixture was warmed to RT. After standing overnight, the same amount of 1,1′-carbonyldiimidazole was again added, and the mixture was stirred for a further 24 h. It was then concentrated and purified by preparative HPLC. 27 mg of the desired compound were obtained.

Aufarbeitung

  1. stirringThe mixture was stirred for 30 min
  2. stirringthe mixture was stirred for a further 24 h
  3. concentrationIt was then concentrated
  4. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-febcc7702b0b4b38a2b62c56417e5015
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722655B2

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