Triethylamine → HCID 18635949, compound

HRID 1639384Notes

Reaction equation

HRID 1639384 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=O)=[O:9])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:35][C@H:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:37].C(N(CC)CC)C>O1CCCC1>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][CH2:13][C:14]([NH:35][C@H:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:37])=[O:16])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Product 1

HCID 18635949HCID 18635949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.00 g (0.006 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid and 1.09 g (0.007 mol) of 1,1'-carbonyldiimidazole are stirred at room temperature for 1.5 hours in 20 ml of tetrahydrofuran and 1.04 g (0.007 mol) of ethyl L-alaninate hydrochloride and 0.94 ml (0.007 mol) of triethylamine are then added thereto. After stirring at room temperature for 2 hours, the mixture is extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with ethyl acetate-methanol (9:1) and then on aluminum oxide with ethyl acetate and subsequent crystallization from ethyl acetate/hexane gives ethyl N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]-L-alaninate as white crystals with melting point 106°.

Workup

  1. extractionthe mixture is extracted with methylene chloride/water
  2. dry with materialdried with magnesium sulfate
  3. distillationthe solvent is distilled in a vacuum
  4. customChromatography on silica gel with ethyl acetate-methanol (9:1) and then on aluminum oxide with ethyl acetate and subsequent crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-27522cf8802f4b85b1eaf5efc8b65b7a
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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