Hydrochloric Acid → 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid

HRID 2101501Notes

Reaction equation

C([O:3][C:4](=[O:28])[CH:5]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:9]=[CH:10][N:11]=1)C.Cl>C1COCC1>[CH2:21]([CH:5]([CH2:6][C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:9]=[CH:10][N:11]=1)[C:4]([OH:28])=[O:3])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl ester (50 mg, 0.12 mmol) in THF (3 mL) was added 6 N HCl (3 mL). The mixture was heated at 75° C. for 14 h with vigorous stirring. The reaction was concentrated in vacuo and the residue washed with Et2O then dried in vacuo to provide the hydrochloride salt of 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid (26 mg, 84%) as a white solid: ESI MS m/z 389 [C20H18Cl2N2O2+H]+.

Workup

concentrationThe reaction was concentrated in vacuo
washthe residue washed with Et2O
customthen dried in vacuo

Sources & evidence

ORD record: ord-946d3019dd144c49a7327ddda7dacc0b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572921B2

Reaction notes

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