Sulfuric Acid → 1,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioate

HRID 395945Notes

Reaction equation

HRID 395945 reaction equation
[H-].[Na+].[C:3]([NH:6][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4].[CH2:18]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33]Br)=[CH:28][CH:27]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].OS(O)(=O)=O>CN(C)C=O.O>[C:3]([NH:6][C:7]([CH2:33][CH2:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:31][CH:30]=1)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 98610072-(4-Octylphenyl)ethyl bromide

Product 1

HCID 98457531,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

60% NaH in oil (9.65 g) is added portionwise to a solution of diethyl acetamidomalonate (58.5 g) in dimethylformamide (240 ml) at such a rate to keep the temperature below 10° C. The resulting mixture is stirred for 90 min., the temperature being allowed to increase to room temperature. To this mixture is added dropwise within 15 min. a solution of 2-(4-octylphenyl)ethyl bromide (19) (40 g) in dimethylformamide (40 ml). The reaction mixture is heated to ca. 80° C. within ca. 25 min. and further stirred for ca. 3-5 hrs. After cooling to room temperature, water (280 ml) is added and the resulting mixture is further stirred until a beige precipitate is formed. The mixture is adjusted to pH 7 with 10% H2SO4. After cooling to ca. 2° C., the residue is filtered, washed with 200 ml water and then recrystallized in heptane to yield compound (8) as colorless crystals. The resulting compound (8) exhibits the same physico-chemical characteristics as indicated in Example 7.

Workup

  1. customthe temperature below 10° C
  2. temperatureThe reaction mixture is heated to ca. 80° C. within ca. 25 min.
  3. stirringfurther stirred for ca. 3-5 hrs
  4. temperatureAfter cooling to room temperature
  5. stirringthe resulting mixture is further stirred until a beige precipitate
  6. customis formed
  7. temperatureAfter cooling to ca. 2° C.
  8. filtrationthe residue is filtered
  9. washwashed with 200 ml water
  10. customrecrystallized in heptane

Sources & evidence

ORD record
ord-8b0ac91d482f4af78f2367fe77a2d83d
Source dataset
uspto-grants-2003_08
Patent number
US06605744B2

Reaction notes

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