Triethylamine → N,N'-Bis(benzyloxycarbonyl)-3-[carboxymethoxyacetyl]-3-azapentane-1,5-diamine

HRID 1067175

Reaction equation

HRID 1067175 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1(=[O:35])[O:34][C:32](=[O:33])[CH2:31][O:30][CH2:29]1.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([C:32](=[O:33])[CH2:31][O:30][CH2:29][C:28]([OH:35])=[O:34])[CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 782321,4-Dioxane-2,6-dioneHCID 4367374N,N''-Di-Z-diethylenetriamine

Product 1

HCID 54008985N,N'-Bis(benzyloxycarbonyl)-3-[carboxymethoxyacetyl]-3-azapentane-1,5-diamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

37.14 g (100 mmol) of the bis(benzyloxycarbonylaminoethyl)-amine described in Example 1a is dissolved in DMF, mixed in an ice bath with 17.4 g (150 mmol) of diglycolic anhydride (Janssen Chimica) and 21 ml (150 mmol) of triethylamine and then stirred overnight at room temperature. The solution is concentrated by evaporation in a vacuum, the residue is taken up in ethyl acetate and shaken out with diluted hydrochloric acid. The organic phase is dried with sodium sulfate and after filtration from drying agent, it is crystallized by adding hexane.

Workup

  1. concentrationThe solution is concentrated by evaporation in a vacuum
  2. stirringshaken out with diluted hydrochloric acid
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. filtrationafter filtration
  5. customfrom drying agent, it
  6. customis crystallized
  7. additionby adding hexane

Sources & evidence

ORD record
ord-47f7d99797424acb961b5b03aec76798
Source dataset
uspto-grants-2001_06
Patent number
US06248306B1

Linked notes

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