2-methyl-2-(phthalimidooxy)thiopropionic acid S-(2-benzothiazolyl) ester → 2-[2-(Aminooxy)-2-methylpropionyl]-1-[(3,4-dihydroxyphenyl)sulphonyl]hydrazine

HRID 846900Notes

Reaction equation

HRID 846900 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][NH2:13])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[OH:8].S1C2C=CC=CC=2N=C1S[C:24](=[O:40])[C:25]([CH3:39])([O:27][N:28]1C(=O)C2=CC=CC=C2C1=O)[CH3:26]>C(#N)C>[NH2:28][O:27][C:25]([CH3:39])([CH3:26])[C:24]([NH:13][NH:12][S:9]([C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)(=[O:10])=[O:11])=[O:40]

Participants

4

Reactant 2

HCID 148526232-methyl-2-(phthalimidooxy)thiopropionic acid S-(2-benzothiazolyl) esterHCID 190224273,4-Dihydroxybenzenesulphonic hydrazide

Product 1

HCID 190224122-[2-(Aminooxy)-2-methylpropionyl]-1-[(3,4-dihydroxyphenyl)sulphonyl]hydrazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 204 mg of 3,4-dihydroxybenzenesulphonic hydrazide and 379 mg of 2-methyl-2-(phthalimidooxy)thiopropionic acid S-(2-benzothiazolyl) ester was heated to 60° C. in 5 ml of acetonitrile for 3 hours. After cooling, any undissolved material was filtered off under suction. The filtrate was freed from solvent in a vacuum and the residue was taken up in 3 ml of ethanol. The suspension was treated with 100 mg of hydrazine hydrate and stirred at 20° C. for 1 hour. A clear solution first resulted, from which a white precipitate separated out. Undissolved material was filtered off and the filtrate was evaporated in a vacuum. The crystalline residue was triturated with 10 ml of 0.1N aqueous hydrochloric acid for 10 minutes and the insoluble material was separated by filtration. The filtrate was adjusted to pH 7 by the addition of 2N aqueous sodium hydroxide solution and chromatographed on MCI gel CHP2OP, with elution being carried out first with 2% aqueous acetic acid and then with water/methanol (9:1, v/v). By evaporation of the product fractions in a vacuum, there was obtained 2-[2-(aminooxy)-2-methylpropionyl]-1-[(3,4-di-hydroxyphenyl)sulphonyl]hydrazine as white crystals of melting point 220° C. (dec.).

Workup

  1. temperatureAfter cooling
  2. filtrationany undissolved material was filtered off under suction
  3. additionThe suspension was treated with 100 mg of hydrazine hydrate
  4. customA clear solution first resulted, from which a white precipitate
  5. customseparated out
  6. filtrationUndissolved material was filtered off
  7. customthe filtrate was evaporated in a vacuum
  8. customThe crystalline residue was triturated with 10 ml of 0.1N aqueous hydrochloric acid for 10 minutes
  9. customthe insoluble material was separated by filtration
  10. additionThe filtrate was adjusted to pH 7 by the addition of 2N aqueous sodium hydroxide solution
  11. customchromatographed on MCI gel CHP2OP, with elution
  12. customBy evaporation of the product fractions in a vacuum

Sources & evidence

ORD record
ord-65acf9bbd3cf4a6d97fc717af00ac0cc
Source dataset
uspto-grants-1992_08
Patent number
US05138066

Reaction notes

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