Hydrochloric Acid → HCID 71115303, compound

HRID 1966093Notes

Reaction equation

[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][NH:18][CH2:19][C:20]([N:29]2[CH2:34][CH2:33][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:31][CH2:30]2)(C(OC)=O)[C:21]([O:23]C)=[O:22])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6].Cl>O1CCCC1.CO.O>[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][NH:18][CH2:19][CH:20]([N:29]2[CH2:30][CH2:31][N:32]([S:35]([CH3:38])(=[O:36])=[O:37])[CH2:33][CH2:34]2)[C:21]([OH:23])=[O:22])(=[O:15])=[O:16])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

Conditions

Temperature: 40 °C

Procedure

1.7 ml (1.7 mmol) of an aqueous solution of sodium hydroxide having a concentration of 1M are added to a solution of 270 mg (0.5 mmol) of dimethyl 2-{[(4-but-2-ynyloxybenzenesulfonyl)methylamino]-methyl}-2-(4-methanesulfonylpiperazin-1-yl)malonate in 7 ml of tetrahydrofuran and 2 ml of methanol. The reaction medium is stirred at 40° C. for 15 h and then brought back to pH=6 by adding an aqueous solution of hydrochloric acid having a concentration of 1M. After evaporation of the solvents under vacuum, the product precipitates. The residue obtained is taken up in 5 ml of water and stirred for 30 min until precipitation occurs. The product is filtered off, rinsed with water and then dried under vacuum. 200 mg (87%) of 3-[(4-but-2-ynyloxybenzenesulfonyl)methylamino]-2-(4-methanesulfonylpiperazin-1-yl)propanoic acid are obtained in the form of a white solid.

Workup

customAfter evaporation of the solvents under vacuum
customthe product precipitates
customThe residue obtained
stirringstirred for 30 min until precipitation
filtrationThe product is filtered off
washrinsed with water
customdried under vacuum

Sources & evidence

ORD record: ord-b279dccfa87746cb998cb08136801dae
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420632B2

Reaction notes

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