Glycine → 2-(1H-imidazol-2-ylamino)acetic acid

HRID 913199Notes

Reaction equation

HRID 913199 reaction equation
[H][H].Cl[C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.Br[C:10]1[N:11]=[CH:12][NH:13][CH:14]=1.[NH2:15][CH2:16][C:17]([OH:19])=[O:18]>O>[NH:8]1[CH:7]=[CH:6][N:5]=[C:4]1[NH:15][CH2:16][C:17]([OH:19])=[O:18].[NH:13]1[CH:14]=[C:10]([NH:15][CH2:16][C:17]([OH:19])=[O:18])[N:11]=[CH:12]1

Participants

7

Reactant 4

HCID 750GlycineHCID 27733282-chloro-1H-imidazoleHCID 178418361HCID 178418361, compoundHCID 178418934HCID 178418934, compound

Product 2

HCID 179368132-(1H-imidazol-2-ylamino)acetic acidHCID 178525864HCID 178525864, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Different N-substituted amino acid derivatives can be used to synthesize other compounds of Formula III wherein Y′ is NHR3 and R3 is not hydrogen. For example, 2-chloro-1H-imidazole or 4-bromo-1H-imidazole can be treated with glycine in water (for example, according to the procedure set forth in European Journal of Medicinal Chemistry (1989), 24(6), 623-5) to form 2-(1H-imidazol-2-ylamino)acetic acid or 2-(1H-imidazol-4-ylamino)acetic acid, respectively, which can then be used to synthesize (2S,4R)-1-(2-(1H-imidazol-2-ylamino)acetyl)-4-benzamidopyrrolidine-2-carboxylic acid or (2S,4R)-1-(2-(1H-imidazol-4-ylamino)acetyl)-4-benzamidopyrrolidine-2-carboxylic acid in a manner similar to Scheme 1. Compounds such as (2S,4R)-4-benzamido-1-(2-(pyridin-2-ylamino)acetyl)pyrrolidine-2-carboxylic acid, (2S,4R)-4-benzamido-1-(2-(pyrimidin-4-ylamino)acetyl)pyrrolidine-2-carboxylic acid, and (2S,4R)-4-benzamido-1-(2-(pyrimidin-2-ylamino)acetyl)pyrrolidine-2-carboxylic acid can be similarly synthesized from 2-(pyridin-2-ylamino)acetic acid, 2-(pyrimidin-4-ylamino)acetic acid, and 2-(pyrimidin-2-ylamino)acetic acid, respectively.

Sources & evidence

ORD record
ord-4f356b75d31947a9862f5357bc3ab015
Source dataset
uspto-grants-2011_09
Patent number
US08026272B2

Reaction notes

Loading…