Triethylamine → HCID 13632751, compound

HRID 1381164Notes

Reaction equation

HRID 1381164 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH2:13].[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([C:22]2[N:26]([CH3:27])[C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24][C:23]=2[CH3:32])=[O:21])=[CH:18][CH:17]=1>C(Cl)(Cl)Cl>[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([C:22]2[N:26]([CH3:27])[C:25]([CH2:28][C:29]([NH:13][CH2:12][C:11]([O:10][CH3:9])=[O:14])=[O:30])=[CH:24][C:23]=2[CH3:32])=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 23323832HCID 23323832, compound

Product 1

HCID 13632751HCID 13632751, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A 22.6 ml (0.16 mole) sample of triethylamine was added to a suspension of 6.78 g (0.054 mole) of glycine methyl ester hydrochloride in 200 ml of spectral grade chloroform. The mixture was cooled to 0° C. and a solution of 16.8 g (0.54 mole) of [5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]-acetyl chloride in 80 ml of chloroform was added slowly. The mixture was stirred at room temperature overnight. The solution was washed successively with dilute hydrochloric acid and water and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. The residue was recrystallized successively from methanol and acetonitrile to give 9.2 g (47% yield) of crystalline methyl N-{[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]-acetyl}-glycinate, m.p. 198°-201° C.

Workup

  1. washThe solution was washed successively with dilute hydrochloric acid and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customThe residue was recrystallized successively from methanol and acetonitrile

Sources & evidence

ORD record
ord-aff73406c9664775bb3b658306f590d5
Source dataset
uspto-grants-1986_04
Patent number
US04585784

Reaction notes

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