Triethylamine → HCID 18669732, compound

HRID 1059006Notes

Reaction equation

HRID 1059006 reaction equation
[C:1]([N:6]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[CH3:7])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18].ClC(OCC)=O.[CH2:30]([N:32](CC)CC(N)C)C>C(Cl)(Cl)Cl>[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH2:21][CH2:30][NH:32][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([N:6]([C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])[CH3:7])=[CH:16][CH:15]=1)[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16643481(2-Aminopropyl)diethylamineHCID 18669726HCID 18669726, compound

Product 1

HCID 18669732HCID 18669732, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a stirred solution of 4-(iso-butyryl-N-methylamino)-benzoic acid (0.088 g) and triethylamine (0.041 g) in chloroform (4 ml) was added a solution of ethyl chlorformate (0.049 g) in chloroform (1 ml). The mixture was stirred under an N2 atmosphere at room temperature for 1½ hours and then cooled to 0° C. N,N-Diethyl-propylenediamine (0.051 g) in chloroform (1 ml) was added and the mixture was stirred over night. The mixture were washed with 0.5 M NaOH(aq) and water. Drying and evaporation of the solvent gave a residue, which was chromatographed on a silica gel column first eluted/washed with ethylacetate and then eluted with ethylacetate-methanol-triethylamine (12:4:1) to yield 0.098 g, of the title product.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture was stirred over night
  3. washThe mixture were washed with 0.5 M NaOH(aq) and water
  4. customDrying
  5. customevaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on a silica gel column
  8. washfirst eluted/washed with ethylacetate
  9. washeluted with ethylacetate-methanol-triethylamine (12:4:1)
  10. customto yield 0.098 g

Sources & evidence

ORD record
ord-d3964e53c0754bc486b69cbf06a8f57a
Source dataset
uspto-grants-2003_02
Patent number
US06518312B2

Reaction notes

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