Hydrochloric Acid → HCID 86648130, compound

HRID 2388242Notes

Reaction equation

HRID 2388242 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[CH2:6]([O:8][C:9](=[O:22])[C:10](=[O:21])[CH:11]([CH3:20])[C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=O)[CH3:7].Cl>O.C(OCC)(=O)C>[CH2:6]([O:8][C:9](=[O:22])[C:10](=[O:21])[CH:11]([CH3:20])[C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[N:4][OH:1])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 67529552HCID 67529552, compound

Product 1

HCID 86648130HCID 86648130, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide (0.99 g, 24.7 mmol) was dissolved in 5.5 mL of water. Hydroxylamine hydrochloride (1.71 g, 24.7 mmol) was added and the reaction mixture was stirred until complete dissolution was achieved. 4-Cyclohexyl-3-methyl-2,4-dioxo-butyric acid ethyl ester (5.15 g, 21.5 mmol) was added and the resulting mixture was stirred at ambient temperature for 16 h. Ethyl acetate (20 mL) and 1M hydrochloric acid (10 mL) was added, and the aqueous layer was extracted with additional ethyl acetate (4×20 mL). The organic layers were combined, dried over MgSO4 and concentrated. The crude oil was purified by chromatography (0-30% EtOAc/hexanes) to give 3.1 g of the title compound. MS: (+) m/z 256.39 (M+1).

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 16 h
  2. extractionthe aqueous layer was extracted with additional ethyl acetate (4×20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude oil was purified by chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e6db7fe6412e40b784d2dc1f1c7a4dc0
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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