Hydrochloric Acid → 2(S)-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoic acid hydrochloride

HRID 910305Notes

Reaction equation

[ClH:1].[CH2:2]([O:4][C@@H:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[N:17]=2)=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:3]>C(O)C>[ClH:1].[CH2:2]([O:4][C@@H:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[N:17]=2)=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

2.5 ml (2.5 mmol) of ethanolic 1M hydrochloric acid solution are added dropwise to a solution of 1.1 g (2.5 mmol) of 2(S)-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoic acid in 2 ml of ethanol, cooled to 0° C. The reaction medium precipitates. After filtration, the precipitate is washed with acetone and with ethyl ether and then dried. After hot recrystallization from a 9/1 acetone/water mixture, 0.6 g (60%) of 2(S)-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoic acid hydrochloride is obtained in the form of a white solid with a melting point of 166° C.

Workup

customThe reaction medium precipitates
filtrationAfter filtration
washthe precipitate is washed with acetone and with ethyl ether
customdried
customAfter hot recrystallization from a 9/1 acetone/water mixture

Sources & evidence

ORD record: ord-bcbe3a5a6eea468fa9820f7ef886067e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022079B2

Reaction notes

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