L-Glutamic Acid → Glu urea imidazole

HRID 77614

Reaction equation

HRID 77614 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:11]1[N:15]=[CH:14][N:13]([C:16]([N:18]2C=NC=C2)=[O:17])[CH:12]=1>>[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7].[NH2:13][C:16]([NH2:18])=[O:17].[NH:13]1[CH:12]=[CH:11][N:15]=[CH:14]1

Participants

3

Reactant 2

HCID 33032L-Glutamic AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 131729281Glu urea imidazole

Procedure

Compounds 217-220, 230 and 231a, b, and c were all prepared in overall yields ranging from 20-40% following the route depicted in Scheme 7. The first step, performed at 0° C. under inert conditions used the di-t-butyl ester of Glutamic acid with CDI in the presence of base to form the intermediate Glu-urea-imidazole derivative 2. This intermediate was activated with MeOTf under basic conditions to afford the methylated imidazole 3, which under inert conditions reacted readily with amines. The tert-butyl ester protecting groups were removed using 20% TFA in DCM for 1 to 4 hour at room temperature. Upon completion of the deprotection, the reactions were concentrated on a rotary evaporator or blown dry with nitrogen and purified on a silica column or recrystallized. The final products were tested in vitro and in vivo.

Workup

  1. customall prepared
  2. customin overall yields
  3. customperformed at 0° C. under inert conditions

Sources & evidence

ORD record
ord-8605a7ee51dc4bbb86a11d9391d936d1
Source dataset
uspto-grants-2014_09
Patent number
US08840865B2

Linked notes

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