Sodium Hydroxide → HCID 66618852, compound

HRID 406329Notes

Reaction equation

HRID 406329 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH3:28])[C:6]([NH:8][NH:9]C(OC(C)(C)C)=O)=[O:7].Cl.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH3:28])[C:6]([NH:8][NH2:9])=[O:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 66618881HCID 66618881, compound

Product 1

HCID 66618852HCID 66618852, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl N′-[5-chloro-2-(5-isopropyl-4-methoxy-2-methylphenyl)pentanoyl]hydrazinecarboxylate (6.1 g) was dissolved in ethyl acetate (50 mL). A 4 N hydrochloric acid-ethyl acetate solution (50 mL) was added and the mixture was stirred at room temperature for 3.5 hours. The reaction solution was made alkaline with a 5 N sodium hydroxide solution under ice-cooling, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (4.4 g). The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b2aca0242bb8457fbb3854e32cbe3aca
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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