Hydrochloric Acid → methyl (S)-3-amino-2-(4-methanesulphonylpiperazin-1-yl)propanoate hydrochloride

HRID 874556Notes

Reaction equation

[ClH:1].C(OC([NH:9][CH2:10][C@H:11]([N:16]1[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]1)[C:12]([O:14][CH3:15])=[O:13])=O)(C)(C)C>C(O)(C)C.CO>[ClH:1].[NH2:9][CH2:10][C@H:11]([N:16]1[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]1)[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 40 °C

Procedure

15 ml of a solution of hydrochloric acid in isopropanol, having a concentration of 5-6N are added dropwise to a solution of 2.7 g (7.4 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-methanesulfonylpiperazin-1-yl)propanoate in 30 ml of methanol. The reaction medium is stirred at 40° C. for 2 h, concentrated under vacuum, and then taken up in 20 ml of methanol and 150 ml of diethyl ether. The product precipitates, and is filtered off under vacuum, rinsed with diethyl ether and then dried under vacuum. 2.3 g (100%) of methyl (S)-3-amino-2-(4-methanesulfonylpiperazin-1-yl)propanoate hydrochloride are obtained in the form of a white solid.

Workup

concentrationconcentrated under vacuum
customThe product precipitates
filtrationis filtered off under vacuum
washrinsed with diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-a4d17b2e9e3e49f3a2bac7c2c437d367
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980897B2

Reaction notes

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