1,1'-Carbonyldiimidazole → Glycine, N-(3-(2-(4-(acetylamino)-1-oxobutyl)-5-chlorophenyl)-1-oxopropyl)-, ethyl ester

HRID 1639386Notes

Reaction equation

HRID 1639386 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.C(N(C(C)C)C(C)C)C.Cl.[NH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>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:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:16])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Product 1

HCID 3078712Glycine, N-(3-(2-(4-(acetylamino)-1-oxobutyl)-5-chlorophenyl)-1-oxopropyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.75 g (0.006 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid and 0.95 g (0.006 mol) of 1,1'-carbonyldiimidazole are stirred at room temperature in 15 ml of tetrahydrofuran and 1.0 ml (0.006 mol) of N-ethyldiisopropylamine and 0.82 g (0.006 mol) of ethyl glycinate hydrochloride are then added thereto. After stirring at room temperature for 1 hour, the solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on aluminum oxide with ethyl acetate-ethanol (9:1) and crystallization from methylene chloride/t-butyl methyl ether gives ethyl N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]-glycinate as white crystals with melting point 96°.

Workup

  1. concentrationthe solution is concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customChromatography on aluminum oxide with ethyl acetate-ethanol (9:1) and crystallization from methylene chloride/t-butyl methyl ether

Sources & evidence

ORD record
ord-f2305c62dbda48fcad64560329a1f81e
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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