1,4-Dioxane hydrochloride → 4-{2-[(Hydrazinocarbonyl)oxy]ethyl}phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylate hydrochloride

HRID 1892488Notes

Reaction equation

HRID 1892488 reaction equation
[NH:1]([C:10]([O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([C:24]2[N:25]=[C:26]([NH:29][C:30](=[O:32])[CH3:31])[S:27][CH:28]=2)=[O:23])=[CH:17][CH:16]=1)=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:39]>ClCCl>[ClH:39].[C:30]([NH:29][C:26]1[S:27][CH:28]=[C:24]([C:22]([O:21][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][O:12][C:10]([NH:1][NH2:2])=[O:11])=[CH:20][CH:19]=2)=[O:23])[N:25]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 866499982-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}oxy)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate

Product 1

HCID 866499994-{2-[(Hydrazinocarbonyl)oxy]ethyl}phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylate hydrochlorideYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}oxy)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate (371.6 mg, 0.800 mmol) in anhydrous dichloromethane (4 ml) was added 4M hydrogen chloride dioxane solution (4 ml). After stirring at room temperature for 2.5 hr, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. The operation was performed twice to remove hydrogen chloride gas azeotropically. The residue was suspended in a mixture of ethanol (5 ml) and ethyl acetate (30 ml), and the suspension was filtered. The filtered product was washed twice with ethyl acetate and dried under reduced pressure to give the title compound (317.7 mg, 0.793 mmol, yield 99.1%) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the concentrated residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customto remove hydrogen chloride gas azeotropically
  5. additionThe residue was suspended in a mixture of ethanol (5 ml) and ethyl acetate (30 ml)
  6. filtrationthe suspension was filtered
  7. washThe filtered product was washed twice with ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-7821bd5d9e124e22b4f268f520468bb9
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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