(Trimethylsilyl)imidazole → 3-(1H-imidazol-1-yl)propanoic acid

HRID 1591071Notes

Reaction equation

HRID 1591071 reaction equation
Cl.[N:2]1([CH2:7][CH2:8][CH2:9][O:10]CC(O)=O)[CH:6]=[CH:5][N:4]=[CH:3]1.C[Si](C)(C)N1C=CN=C1.C[Si]([O:28]C(=O)C(Cl)C)(C)C>>[N:2]1([CH2:7][CH2:8][C:9]([OH:10])=[O:28])[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 28925(Trimethylsilyl)imidazoleHCID 197663206-(Imidazol-1-yl)-3-oxa-hexanoic acid-hydrochlorideHCID 86746752Chloropropionic acid-trimethylsilyl ester

Product 1

HCID 27947183-(1H-imidazol-1-yl)propanoic acid

Procedure

The 6-(imidazol-1-yl)-3-oxa-hexanoic acid-hydrochloride used as the starting material is prepared in the following manner: 1-trimethylsilylimidazole (b.p.20 : 117°-120° C.) is reacted with chloropropionic acid-trimethylsilyl ester (b.p.1013 : 172°-175° C.) with simultaneous saponification of the esters to form 3-(imidazol-1-yl)-propionic acid (m.p.: 148°-150° C.). Reaction with trimethylchlorosilane in ethanol leads to the corresponding ethyl ester-hydrochloride from which the free 3-(imidazol-1-yl)-propionic acid-ethyl ester (oil) was obtained with 2N sodium hydroxide solution. The 1-(imidazol-1-yl)-3-propanol (oil) obtained after reduction with lithium aluminium hydride is allowed to react with ethyl bromoacetate in dimethyl formamide in the presence of sodium hydride to form 6-(imidazol-1-yl)-3-oxa-hexanoic acid ethyl ester (oil) which is subsequently saponified with 3N hydrochloric acid to form the desired acid.

Workup

  1. customis prepared in the following manner

Sources & evidence

ORD record
ord-e3f1384c1bbc463abf46a3fd77a7c93d
Source dataset
uspto-grants-1993_04
Patent number
US05206253

Reaction notes

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