Reaktion #1362429

ord-614acc42da99495b951a41d298e25921

Reaktionsgleichung

N[C@@]1(C(=O)O)CC(=O)[C@H]2[C@H](C(=O)O)[C@H]21

(1S*,2S*,5R*,6R*)-2-amino-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

N[C@]1(C(=O)O)C[C@H](F)[C@@H]2[C@@H](C(=O)O)[C@@H]21

(1S*,2R*,4S*,5S*,6S*)-2-amino-4-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

C=C1C[C@@](N)(C(=O)O)[C@H]2[C@@H]1[C@@H]2C(=O)O

(1S*,2S*,5R*,6S*)-2-amino-4-methylenebicyclo[3.1.0]hexane-2,6-dicarboxylic acid

glutamate

→

2-amino-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Edukte

(1S*,2S*,5R*,6R*)-2-amino-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

—

(1S*,2S-,5R*,6S*)-2-amino-4-Z-carboxymethylenebicyclo-[3.1.0]hexane-2,6-dicarboxylic acid

—

(1S*,2S*,5R*,6R*)-2-amino-4-[syn] -hydroximinobicyclo-[3.1.0]hexane-2,6-dicarboxylic acid

(1S*,2R*,4S*,5S*,6S*)-2-amino-4-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

(1S*,2S*,5R*,6S*)-2-amino-4-methylenebicyclo[3.1.0]hexane-2,6-dicarboxylic acid

glutamate

—

(1S*,2S*,5R*,6R*)-2-amino-4-[anti]-hydroximinobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Vorschrift

Particularly preferred compounds of formula I are (1S*,2S*,5R*,6R*)-2-amino-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylic acid; (1S*,2S*,5R*,6R*)-2-amino-4-[anti]-hydroximinobicyclo[3.1.0]hexane-2,6-dicarboxylic acid; (1S*,2S*,5R*,6R*)-2-amino-4-[syn] -hydroximinobicyclo-[3.1.0]hexane-2,6-dicarboxylic acid; (1S*,2R*,4S*,5S*,6S*)-2-amino-4-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid; (1S*,2S-,5R*,6S*)-2-amino-4-Z-carboxymethylenebicyclo-[3.1.0]hexane-2,6-dicarboxylic acid and (1S*,2S*,5R*,6S*)-2-amino-4-methylenebicyclo[3.1.0]hexane-2,6-dicarboxylic acid. These compounds have been found to process especially high potency as metabotropic glutamate receptor modulators.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06160009uspto-grants-2000_12