Water → tert-butyl N'-[5-chloro-2-(4-fluorophenyl)-2-methoxypentanoyl]hydrazinecarboxylate

HRID 1009402Notes

Reaction equation

HRID 1009402 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][CH2:8][CH2:9][CH2:10][C:11]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([O:15][CH3:16])[C:12]([OH:14])=O.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[NH:25][NH2:26].O>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[Cl:7][CH2:8][CH2:9][CH2:10][C:11]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([O:15][CH3:16])[C:12]([NH:26][NH:25][C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:14]

Participants

8

Reactant 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 70091tert-Butyl carbazateHCID 670671515-Chloro-2-(4-fluorophenyl)-2-methoxyvaleric acid

Product 1

HCID 67067169tert-butyl N'-[5-chloro-2-(4-fluorophenyl)-2-methoxypentanoyl]hydrazinecarboxylateYield 58%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Oxalyl chloride (44 μL) was added a mixed solution of 5-chloro-2-(4-fluorophenyl)-2-methoxyvaleric acid (108 mg) in methylene chloride (1 mL) and DMF (1 drop) under ice-cooling, and then the reaction solution was stirred at room temperature for 30 minutes. The acid chloride solution was added dropwise to a solution of tert-butyl carbazate (82 mg) and TEA (0.3 mL) in methylene chloride (2 mL) under ice-cooling, and the reaction solution was stirred at the same temperature for 10 minutes and at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with 1 N hydrochloric acid, water, a saturated sodium bicarbonate solution and brine. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 90 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe reaction solution was stirred at the same temperature for 10 minutes and at room temperature for 30 minutes
  4. customthe organic layer was separated
  5. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water
  6. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-423690a84cf44e8d97576ec2c3a17bb9
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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