L-glutamate(2-) → HCID 22119095, compound

HRID 1275247Notes

Reaction equation

HRID 1275247 reaction equation
[NH2:1][C@@:2]1([C:12]([OH:14])=[O:13])[CH2:7][C:6](=[O:8])[C@@H:5]2[C@H:3]1[C@H:4]2[C:9]([OH:11])=[O:10].N[C@]1(C(O)=O)C[C@H](F)[C@H]2[C@@H]1[C@@H]2C(O)=O.N[C@@]1(C(O)=O)CC(=C)[C@@H]2[C@H]1[C@H]2C(O)=O.N[C@H](C([O-])=O)CCC([O-])=O>>[NH2:1][C:2]1([C:12]([OH:14])=[O:13])[CH2:7][CH:6]([OH:8])[CH:5]2[CH:3]1[CH:4]2[C:9]([OH:11])=[O:10]

Participants

5

Reactant 4

HCID 5460544L-glutamate(2-)HCID 9794208(1S,2S,5R,6R)-2-amino-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylic acidHCID 9958635Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-4-fluoro-, (1S,2R,4S,5S,6S)- (9CI)HCID 70051926HCID 70051926, compound

Product 1

HCID 22119095HCID 22119095, compound

Procedure

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.

Sources & evidence

ORD record
ord-614acc42da99495b951a41d298e25921
Source dataset
uspto-grants-2000_12
Patent number
US06160009

Reaction notes

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