Reaktion #543910

ord-b2ab848cf9b44197b05f6964eb4950f0

Reaktionsgleichung

CC(C)(C)OC(=O)N1[C@H]2CC[C@H]([C@H](O)C2)[C@H]1C(=O)O

(1S,3S,4S,5R)-2-(tert-butoxycarbonyl)-5-hydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid

(1S,3S,4S,5R)-2-(tert-Butoxycarbonyl)-5-hydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid

(2S)-2-pyrrolidinecarboxamide

1-hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

N,N-diisopropylethylamine

→

CC(C)(C)OC(=O)N1[C@H]2CC[C@H]([C@H](O)C2)[C@H]1C(=O)N1CCC[C@H]1C(N)=O

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

Edukte

(1S,3S,4S,5R)-2-(tert-butoxycarbonyl)-5-hydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid

(1S,3S,4S,5R)-2-(tert-Butoxycarbonyl)-5-hydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid

(2S)-2-pyrrolidinecarboxamide

1-hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

N,N-diisopropylethylamine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
Temperaturwith cooling on an ice bath
2
Sonstigethe ice bath was removed

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07186731B2uspto-grants-2007_03