Sodium Hydroxide → HCID 178512521, compound

HRID 1415673Notes

Reaction equation

HRID 1415673 reaction equation
C([NH:8][C:9](=[NH:33])[NH:10][C:11]1[CH:32]=[CH:31][C:14]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[C:19](=[O:30])[CH2:18]2)=[O:16])=[CH:13][CH:12]=1)(OC(C)(C)C)=O.[OH-].[Na+]>O1CCOCC1>[NH:10]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C:19](=[O:30])[CH2:18]2)=[O:16])=[CH:31][CH:32]=1)[C:9]([NH2:33])=[NH:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178471841HCID 178471841, compound

Product 1

HCID 178512521HCID 178512521, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 10 g of ethyl 3-(4-(4-(3-BOC-guanidino)benzoyl)-2-oxopiperazin-1-yl)propionate (m.p. 143°; FAB 462; obtainable by condensing 4-(3-BOC-guanidino)benzoic acid with ethyl 3-(2-oxopiperazin-1-yl)propionate), 400 ml of dioxane and 56 ml of 1 N aqueous NaOH solution is stirred for 5 hours at 20°. It is evaporated, the residue is dissolved in water, the solution is washed several times with ethyl acetate, and HCl is added to pH 4. Extraction is carried out with ethyl acetate, the extract is dried and evaporated, the resulting crude 3-(4-(4-(3-BOC-guanidino)benzoyl)-2-oxopiperazin-1-yl)propionic acid is dissolved in 200 ml of 4 N HCl in dioxane and the solution is stirred for 3 hours at 20° and worked up in conventional manner to give 3-(4-(4-guanidinobenzoyl)-2-oxopiperazin-1-yl)propionic acid, m.p. 110° (decomposition).

Workup

  1. customIt is evaporated
  2. dissolutionthe residue is dissolved in water
  3. washthe solution is washed several times with ethyl acetate, and HCl
  4. additionis added to pH 4
  5. extractionExtraction
  6. customthe extract is dried
  7. customevaporated
  8. dissolutionthe resulting crude 3-(4-(4-(3-BOC-guanidino)benzoyl)-2-oxopiperazin-1-yl)propionic acid is dissolved in 200 ml of 4 N HCl in dioxane
  9. stirringthe solution is stirred for 3 hours at 20°

Sources & evidence

ORD record
ord-c9403eaf652949eea58869b3680bbfdb
Source dataset
uspto-grants-1999_06
Patent number
US05908843

Reaction notes

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