Hydrochloric Acid → HCID 71115303, compound

HRID 2202166Notes

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-4fbf76e242b34a70a6636239dc060fc5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365529B2

Reaction notes

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