1,1'-Carbonyldiimidazole → Carbamoylmethyl 2-(4-acetamidobutyryl)-5-chlorohydrocinnamate

HRID 1639388Notes

Reaction equation

HRID 1639388 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:15])=[O:9])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:34]([NH2:38])(=[O:37])[CH2:35]O>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]([O:16][CH2:35][C:34](=[O:37])[NH2:38])=[O:15])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 690212-HydroxyacetamideHCID 19833127HCID 19833127, compound

Product 1

HCID 19833170Carbamoylmethyl 2-(4-acetamidobutyryl)-5-chlorohydrocinnamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 15.5 g (0.05 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid and 8.50 g (0.052 mol) of 1,1'-carbonyldiimidazole in 350 ml of tetrahydrofuran is stirred at room temperature for 2 hours and 4.00 g (0.052 mol) of glycolamide are added thereto. After stirring at room temperature overnight, the solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with methylene chloride-methanol (20:1) and crystallization from ethyl acetate/ether gives carbamoylmethyl 2-(4-acetamidobutyryl)-5-chlorohydrocinnamate as white crystals with melting point 114°-116°.

Workup

  1. stirringAfter stirring at room temperature overnight
  2. concentrationthe solution is concentrated
  3. extractionextracted with methylene chloride/water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent is distilled in a vacuum
  6. customChromatography on silica gel with methylene chloride-methanol (20:1) and crystallization from ethyl acetate/ether

Sources & evidence

ORD record
ord-3c659eb5d04e40d692f60af25b57ea7d
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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