Diisopropylethylamine → Tert-Butyl (1S,3S,4S,5R)-3-{[(2S)-2-aminocarbonyl-1-pyrrolidinyl]carbonyl}-5-hydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate

HRID 456728

Reaktionsgleichung

Reaktionsgleichung von HRID 456728
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14](O)=[O:15])[C@@H:12]2[CH2:17][CH2:18][C@H:9]1[CH2:10][C@H:11]2[OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[C:25]([NH2:27])=[O:26].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>>[NH2:27][C:25]([C@@H:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:14]([C@@H:13]1[C@@H:12]2[CH2:17][CH2:18][C@@H:9]([CH2:10][C@H:11]2[OH:19])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])=[O:26]

Komponenten

6

Edukt 5

HCID 81531DiisopropylethylamineHCID 111306L-ProlinamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69135461(1S,3S,4S,5R)-2-tert-butoxycarbonyl-5-hydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid

Produkt 1

HCID 86598890Tert-Butyl (1S,3S,4S,5R)-3-{[(2S)-2-aminocarbonyl-1-pyrrolidinyl]carbonyl}-5-hydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate

Versuchsvorschrift

To a solution of (1S,3S,4S,5R)-2-(tert-butoxycarbonyl)-5-hydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid obtained in Example 2-5 (4.05 g), (2S)-2-pyrrolidinecarboxamide (1.77 g) and 1-hydroxybenzotriazole hydrate (1.68 g), were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.15 g) and N,N-diisopropylethylamine (5.2 mL) with cooling on an ice bath. After 5 minutes, the ice bath was removed and the mixture was stirred overnight at room temperature.

Aufarbeitung

  1. temperaturewith cooling on an ice bath
  2. customthe ice bath was removed

Quellen und Nachweise

ORD-Eintrag
ord-b2ab848cf9b44197b05f6964eb4950f0
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186731B2

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