Hydrochloric Acid → Methyl (S)-3-amino-2-(4-methanesulfonylpiperazin-1-yl)propanoate dihydrochloride

HRID 472121Notes

Reaction equation

HRID 472121 reaction equation
C(OC([NH:8][CH2:9][C@H:10]([N:15]1[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]1)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.[ClH:25]>CO.C(O)(C)C.C(OCC)C>[ClH:25].[ClH:25].[NH2:8][CH2:9][C@H:10]([N:15]1[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]1)[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67056930methyl (S)-3-tert-butoxycarbonylamino-2-(4-methanesulfonylpiperazin-1-yl)propanoate

Product 1

HCID 86675013Methyl (S)-3-amino-2-(4-methanesulfonylpiperazin-1-yl)propanoate dihydrochlorideYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4 g (11 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-methanesulfonylpiperazin-1-yl)propanoate (prepared as described in example 2.4) in 40 ml of methanol and 20 ml of a solution of hydrochloric acid in isopropanol, having a concentration of 5 or 6M, is stirred at 40° C. for 18 h and then concentrated under vacuum. The residue obtained is taken up in 200 ml of diethyl ether, filtered, and then dried under vacuum. 3.5 g (94%) of methyl (S)-3-amino-2-(4-methanesulfonylpiperazin-1-yl)propanoate dihydrochloride are obtained in the form of a beige solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue obtained
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0970af5d7bbc4fcba0b190fb10ddabf1
Source dataset
uspto-grants-2014_01
Patent number
US08633196B2

Reaction notes

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