Triethylamine → HCID 86741987, compound

HRID 4129Notes

Reaction equation

HRID 4129 reaction equation
[Cl-].[CH3:2]/[C:3](=[C:9](/[CH3:13])\[C:10]([O-:12])=[O:11])/[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:14][C:15]([CH3:22])([CH:19]([CH3:21])[CH3:20])[C:16]([NH2:18])=[O:17].C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([O:6][C:4](=[O:5])/[C:3](/[CH3:2])=[C:9](\[CH3:13])/[C:10]([O-:12])=[O:11])[CH3:8].[NH2:18][C:16]([C:15]([NH-:14])([CH3:22])[CH:19]([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97937732-Amino-2,3-dimethylbutanamideHCID 20152698HCID 20152698, compound

Product 1

HCID 86741987HCID 86741987, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13 g of monoethyl 2,3-dimethylfumarate chloride in 20 ml of methylene chloride was added dropwise, while stirring and cooling with ice, to a solution of 12 g of 2-amino-2,3-dimethyl-butyric acid amide and 12 ml of triethylamine in 80 ml of methylene chloride. The mixture was stirred for 2 hours at room temperature, the resulting solution was extracted with water, with 2N hydrochloric acid and again with water, then dried and evaporated. The residue was triturated with diethyl ether, suction-filtered and recrystallized from a little ethanol. 8.0 g (41% of theory) of monoethyl-2,3-dimethylfumarate-N-(1-aminocarbonyl-1-methylisobutyl)-amide were obtained, m.p. 122°-125° C.

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature
  2. extractionthe resulting solution was extracted with water, with 2N hydrochloric acid and again with water
  3. customdried
  4. customevaporated
  5. customThe residue was triturated with diethyl ether
  6. filtrationsuction-filtered
  7. customrecrystallized from a little ethanol

Sources & evidence

ORD record
ord-1726b250b80e416d94f4df3e349e6e44
Source dataset
uspto-grants-1988_02
Patent number
US04723989

Reaction notes

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