Triethylamine → HCID 54353084, compound

HRID 2166607Notes

Reaction equation

HRID 2166607 reaction equation
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=O.[CH2:10]([K])[CH3:11].C(Cl)(=O)C(Cl)=O.[C:19]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].C(N(CC)CC)C>C(OCC)C>[C:19]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:3](=[O:5])[CH:2]1[O:1][CH:6]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2783677Benzyl N-(4-aminobutyl)carbamateHCID 178461626HCID 178461626, compound

Product 1

HCID 54353084HCID 54353084, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of monoethyl potassium epoxysuccinate (0.77 g) in ethyl ether (30 ml), oxalyl chloride (0.75 g) in ethyl ether was added dropwise with stirring under ice-cooling and the mixture was stirred for an hour at room temperature. To the resulting mixture, a solution of N-carbobenzoxy 1,4-diaminobutane (1.1 g) and triethylamine (0.48 g) in ethyl ether was added dropwise with stirring under ice-cooling, and the mixture was stirred for an additional hour at room temperature. The resulting precipitate was filtered off and the filtrate was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography using benzene as a developer. The crude crystals thus obtained were recrystallized from acetone-n-hexane to give 0.97 g of ethyl N-carbobenzoxyaminobutyl-2,3-epoxysuccinamate (Compound No. 68) as colorless plates melting at 94°-95° C.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe mixture was stirred for an hour at room temperature
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred for an additional hour at room temperature
  7. filtrationThe resulting precipitate was filtered off
  8. washthe filtrate was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated to dryness
  11. customThe residue was purified by silica gel column chromatography
  12. customThe crude crystals thus obtained
  13. customwere recrystallized from acetone-n-hexane

Sources & evidence

ORD record
ord-439268d520144f7b97b94c870eef5013
Source dataset
uspto-grants-1983_06
Patent number
US04387238

Reaction notes

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