1,1'-Carbonyldiimidazole → L-Glutamic acid, N-(3-(2-(4-(acetylamino)-1-oxobutyl)-5-chlorophenyl)-1-oxopropyl)-, diethyl ester

HRID 1639385Notes

Reaction equation

HRID 1639385 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:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].C(N(C(C)C)C(C)C)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:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:16])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 73960Glutamic acid diethyl ester hydrochlorideHCID 81531DiisopropylethylamineHCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Product 1

HCID 3078714L-Glutamic acid, N-(3-(2-(4-(acetylamino)-1-oxobutyl)-5-chlorophenyl)-1-oxopropyl)-, diethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.10 g (0.01 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid and 1.70 g (0.015 mol) of 1,1'-carbonyldiimidazole are stirred at room temperature for 1 hour in 50 ml of tetrahydrofuran and 2.51 g (0.011 mol) of diethyl L-glutamate hydrochloride and 1.8 ml (0.011 mol) of N-ethyldiisopropylamine are then added thereto. After stirring at room temperature for 2 hours the solution is concentrated, extracted with methylene chloride/water, dried with sodium sulfate and the solvent is distilled in a vacuum. Chromatography on aluminum oxide with methylene chloride-methanol (97:3) and crystallization from ethyl acetate/hexane gives diethyl N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]-L-glutamate as white crystals with melting point 109°-111°.

Workup

  1. concentrationis concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with sodium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customChromatography on aluminum oxide with methylene chloride-methanol (97:3) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d0ea77cff94f4fb48f81520a4d4d33b7
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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