Sodium Hydroxide → N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]glycine

HRID 1639394Notes

Reaction equation

HRID 1639394 reaction equation
[OH-].[Na+].[C:3]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:13]=1[CH2:14][CH2:15][C:16]([NH:18][CH2:19][C:20]([O:22]CC)=[O:21])=[O:17])=[O:11])(=[O:5])[CH3:4]>O1CCCC1>[C:3]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:13]=1[CH2:14][CH2:15][C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])=[O:11])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3078712Glycine, N-(3-(2-(4-(acetylamino)-1-oxobutyl)-5-chlorophenyl)-1-oxopropyl)-, ethyl ester

Product 1

HCID 19838947N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]glycine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 ml of 2N sodium hydroxide solution are added to a solution of 1.50 g (0.004 mol) of ethyl N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]glycinate in 15 ml of tetrahydrofuran and the mixture is stirred at room temperature for 1 hour. After acidification with 17 ml of 2N hydrochloric acid, the mixture is extracted with ethyl acetate/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Recrystallization from ethyl acetate/ether yields N-[2-(4-acetamidobutyryl)-5-chlorohydrocinnamoyl]glycine as white crystals with melting point 88°-89°.

Workup

  1. extractionAfter acidification with 17 ml of 2N hydrochloric acid, the mixture is extracted with ethyl acetate/water
  2. dry with materialdried with magnesium sulfate
  3. distillationthe solvent is distilled in a vacuum
  4. customRecrystallization from ethyl acetate/ether

Sources & evidence

ORD record
ord-2c5993a40e184717ae3127ac009c8f5e
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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