Sodium Hydroxide → HCID 178458303, compound

HRID 363370Notes

Reaction equation

HRID 363370 reaction equation
[C:1]([CH2:5][C:6](OCC)=[O:7])(=O)[CH2:2][CH3:3].CS(O)(=O)=O.[CH2:16]([O:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH2:24])=[NH:23])[CH2:17][CH3:18].[OH-].[Na+]>O.C(O)C>[CH2:2]([C:1]1[CH:5]=[C:6]([OH:7])[N:24]=[C:22]([C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[O:19][CH2:16][CH2:17][CH3:18])[N:23]=1)[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 78656Ethyl 3-oxovalerateHCID 22462369HCID 22462369, compound

Product 1

HCID 178458303HCID 178458303, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl propionylacetate (0.79 g), 2-propoxybenzamidine methanesulfonate (1.45 g) and sodium hydroxide (0.60 g) in water (5 ml) and ethanol (5 ml) was stirred at ambient temperature for 22 hours. Most of the solvent was removed under reduced pressure and water (20 ml) was added. The mixture was acidified to pH 2 with concentrated hydrochloric acid and then extracted with chloroform (3×30 ml). The combined extracts were washed with dilute acetic acid, dried (magnesium sulfate) and evaporated under reduced pressure to yield a residue which was recrystallized twice from ether to yield the title compound, 373 mg. m.p. 97°-98.5° C.

Workup

  1. customMost of the solvent was removed under reduced pressure and water (20 ml)
  2. additionwas added
  3. extractionextracted with chloroform (3×30 ml)
  4. washThe combined extracts were washed with dilute acetic acid
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customto yield a residue which
  8. customwas recrystallized twice from ether

Sources & evidence

ORD record
ord-7c65705df35b43f0b545e421f0d151ac
Source dataset
uspto-grants-1999_02
Patent number
US05874440

Reaction notes

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