Hydrochloric Acid → n-(o-(3-Maleinimidobenzoyl)-2-hydroxyethyl)-1,2-diaminoethane dihydrochloride

HRID 382254Notes

Reaction equation

HRID 382254 reaction equation
[C:1]1(=[O:36])[N:5]([C:6]2[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=2)[C:9]([O:11][CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][NH:17]C(OC(C)(C)C)=O)=[O:10])[C:4](=[O:35])[CH:3]=[CH:2]1.[ClH:37]>C(OCC)C>[ClH:37].[ClH:37].[C:4]1(=[O:35])[N:5]([C:6]2[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=2)[C:9]([O:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:1](=[O:36])[CH:2]=[CH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 22741540n-(o-(3-Maleinimidobenzoyl)-2-hydroxyethyl)-n,n'-bis-tertiarybutyloxycarbonyl-1,2-diaminoethane

Product 1

HCID 22741529n-(o-(3-Maleinimidobenzoyl)-2-hydroxyethyl)-1,2-diaminoethane dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6 g (11.93 mmol) of N-(O-(3-maleinimidobenzoyl)-2-hydroxyethyl)-N,N′-bis-tertiarybutyloxycarbonyl-1,2-diaminoethane are diluted with 60 ml (5 eq) of a 1 M solution of HCl in diethylether while stirring at room temperature. After 48 h of stirring at room temperature, the fine-crystallinic precipitate is suctioned off over a G4 glass frit, freed of the HCl residues through multiple washing with anhydrous ether and dried under a vacuum. Obtained are 3.0 g (7.98 mmol) of the product as a fine-powdery yellow solid, corresponding to 66.9% of the theoretically possible yield. Elementary analysis for C15H19N3O4Cl2 (375.9 g/mol); calculated: C: 47.89%, H: 5.05%, N: 11.17%, Cl: 18.86%; found: C: 46.97%, H: 5.42%, N: 10.03%, Cl: 17.63%.

Workup

  1. stirringAfter 48 h of stirring at room temperature
  2. washthrough multiple washing with anhydrous ether
  3. customdried under a vacuum
  4. customObtained

Sources & evidence

ORD record
ord-2b9a6a591d6143eaa34c68897f81463e
Source dataset
uspto-grants-2001_10
Patent number
US06310039B1

Reaction notes

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