Hydrochloric Acid → 3-(4-But-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid

HRID 517491Notes

Reaction equation

HRID 517491 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:36]=[CH:35][C:11]([C:12]([NH:14][CH2:15][C:16]([N:25]2[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:27][CH2:26]2)(C(OC)=O)[C:17]([O:19]C)=[O:18])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6].Cl>O1CCCC1.CO.C(OCC)(=O)C>[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][CH2:15][CH:16]([N:25]2[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:27][CH2:26]2)[C:17]([OH:19])=[O:18])=[O:13])=[CH:35][CH:36]=1)[C:4]#[C:5][CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67056992Dimethyl 2-[(4-but-2-ynyloxybenzoylamino)methyl]-2-(4-methanesulphonylpiperazin-1-yl)malonate

Product 1

HCID 680883553-(4-But-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acidYield 35.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 ml (0.5 mmol) of an aqueous solution of sodium hydroxide having a concentration of 1N are added to a solution of 100 mg (0.2 mmol) of dimethyl 2-[(4-but-2-ynyloxybenzoylamino)methyl]-2-(4-methanesulphonylpiperazin-1-yl)malonate in 4 ml of tetrahydrofuran and 1 ml of methanol. The reaction medium is stirred at ambient temperature for 48 h then hydrolysed, diluted with ethyl acetate and brought to pH=6 with an aqueous solution of hydrochloric acid having a concentration of 1N. After extraction with ethyl acetate, the organic phase is washed with water then with a saturated aqueous solution of sodium chloride. After drying over magnesium sulphate and filtering, the solvent is concentrated under vacuum. The crude product obtained is purified by recrystallization in ethyl acetate. 30 mg (32%) of 3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid are obtained in the form of a white solid.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialAfter drying over magnesium sulphate
  4. filtrationfiltering
  5. concentrationthe solvent is concentrated under vacuum
  6. customThe crude product obtained
  7. customis purified by recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-e32c65c885eb43888833070aa19d3df1
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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