Trifluoroacetic acid → 5-Chloro-2-cyclopropyl-valeric acid hydrazide

HRID 546694Notes

Reaction equation

HRID 546694 reaction equation
FC(F)(F)C(O)=O.[Cl:8][CH2:9][CH2:10][CH2:11][CH:12]([CH:24]1[CH2:26][CH2:25]1)[C:13]([NH:15][NH:16]C(OC(C)(C)C)=O)=[O:14].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(Cl)Cl>[Cl:8][CH2:9][CH2:10][CH2:11][CH:12]([CH:24]1[CH2:25][CH2:26]1)[C:13]([NH:15][NH2:16])=[O:14]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 66839486tert-butyl N'-(5-chloro-2-cyclopropyl-pentanoyl)-hydrazinecarboxylate

Product 1

HCID 668394715-Chloro-2-cyclopropyl-valeric acid hydrazideYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 ml) was added to a solution of tert-butyl N′-(5-chloro-2-cyclopropyl-pentanoyl)-hydrazinecarboxylate (208 mg) in methylene chloride (1 ml) under ice-cooling, and then the reaction solution was stirred at room temperature for two hours. A saturated sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine. The combined aqueous layers were reextracted with ethyl acetate (twice). The combined organic layers were dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 127 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9546f6b11fa249eca34854bf8d1c10ef
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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