Hydrochloric Acid → HCID 10402973, compound

HRID 2379535Notes

Reaction equation

HRID 2379535 reaction equation
[OH-].[Na+].[CH3:3]/[C:4](/[CH2:16][CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH:5]\[CH2:6][NH:7][C:8](=[O:15])[CH2:9][C:10]([O:12]CC)=[O:11].Cl>C(O)C.[Cl-].[Na+].O>[CH3:3]/[C:4](/[CH2:16][CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH:5]\[CH2:6][NH:7][C:8](=[O:15])[CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10314913HCID 10314913, compound

Product 1

HCID 10402973HCID 10402973, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydroxide (1N, 0.68 mL, 0.68 mmol) was added to a stirred solution of ethyl 3-[(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienylamino]-3-oxopropionate (0.115 g, 0.34 mmol) in ethanol (2 mL) at 0° C. The resulting mixture was stirred at 0° C. for 5 minutes, then warmed to room temperature and stirred for 0.5 hours. The reaction mixture was poured into brine, acidified with hydrochloric acid (5%) and extracted with ethyl acetate. The extract was washed with brine, dried, filtered and evaporated to afford the title compound (80 mg, 0.26 mmol, 76%) as a gum.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 0.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b83423d0e0aa422db69bfddb9378d253
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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