Triethylamine → HCID 19833167, compound

HRID 1639393Notes

Reaction equation

HRID 1639393 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:17]=1[CH2:18][CH2:19][C:20]([OH:22])=O)=[O:15])=[O:9])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].C(N(CC)CC)C>O1CCCC1>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:17]=1[CH2:18][CH2:19][C:20]([NH:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:22])=[O:15])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2723640Glycine ethyl ester, hydrochlorideHCID 19833168HCID 19833168, compound

Product 1

HCID 19833167HCID 19833167, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.00 g (0.015 mol) of 2-[4-(4-acetamidobutyramido)butyryl]-5-chlorohydrocinnamic acid and 2.57 g (0.016 mol) of 1,1'-carbonyldiimidazole are stirred at room temperature for 1.5 hours in 60 ml of tetrahydrofuran and 2.22 g (0.016 mol) of ethyl glycinate hydrochloride and 2.2 ml (0.016 mol) of triethylamine are 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 silica gel with ethyl acetate-ethanol (9:1) and crystallization from methanol-ether gives ethyl N-[2-[4-(4-acetamidobutyramido)butyryl]-5-chlorohydrocinnamoyl]glycinate as white crystals with melting point 94°-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 silica gel with ethyl acetate-ethanol (9:1) and crystallization from methanol-ether

Sources & evidence

ORD record
ord-c223f7855d2f427983ca5089f526fdbf
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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