Water → 4-[2-({[2-(Tert-butoxycarbonyl)hydrazino]carbonyl}amino)ethyl]phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylate

HRID 1892534Notes

Reaction equation

HRID 1892534 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH:34][C:35]([NH:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:36])=[CH:28][CH:27]=1.O>C(OCC)(=O)C>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][NH:34][C:35]([NH:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:36])=[CH:30][CH:31]=2)=[O:11])[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 8401132-Acetamido-1,3-thiazole-4-carboxylic acidHCID 58112047Tert-butyl 2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}hydrazinecarboxylate

Product 1

HCID 866500414-[2-({[2-(Tert-butoxycarbonyl)hydrazino]carbonyl}amino)ethyl]phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylateYield 44.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (559.5 mg, 3.005 mmol) in anhydrous N,N-5 dimethylformamide (10 ml) was added 1,1′-carbonyldiimidazole (534.2 mg, 3.294 mmol), and the mixture was stirred at 50° C. for 2 hr. tert-Butyl 2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}hydrazinecarboxylate (591.6 mg, 2.003 mmol) was added, and the mixture was stirred at 50° C. for 24 hr and at room temperature for 17 hr. Water (50 ml) and ethyl acetate (50 ml) were added to the reaction mixture and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with 0.5M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Methanol (20 ml) and tert-butyl methyl ether (40 ml) were added to the residue and the precipitated solid was collected by filtration and dried under reduced pressure to give 4-[2-({[2-(tert-butoxycarbonyl)hydrazino]carbonyl}amino)ethyl]phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylate (417.7 mg, 0.890 mmol, yield 44.5%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 50° C. for 24 hr and at room temperature for 17 hr
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with 0.5M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionMethanol (20 ml) and tert-butyl methyl ether (40 ml) were added to the residue
  9. filtrationthe precipitated solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-b4f5f45cfe574cabb2290d5adf5db261
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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