Triethylamine → HCID 178501495, compound

HRID 1590123Notes

Reaction equation

HRID 1590123 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178419105HCID 178419105, compound

Product 1

HCID 178501495HCID 178501495, compoundYield 124.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(benzyloxycarbonyl)-L-2-aminoxy-3-phenylpropionic acid (3.09 g), L-histidine methyl ester dihydrochloride (2.42 g), N-hydroxy-benzotriazole (1.35 g), triethylamine (2.8 ml) and dimethylformamide(20 ml) is added dicyclohexylcarbodiimide (2.1 g) under ice-cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure to remove solvent, and ethyl acetate is added to the residue. Insoluble materials are filtered off. The filtrate is washed with an aqueous sodium bicarbonate solution and water, dried, and then concentrated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chloroformethyl acetate=12:1) and crystallized with hexane to give N [N-(benzyloxycarbonyl)-L-2-aminoxy 3-phenylpropionyl] -L-histidine methyl ester(2.1 g) as white powder. KBr

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customto remove solvent, and ethyl acetate
  4. additionis added to the residue
  5. filtrationInsoluble materials are filtered off
  6. washThe filtrate is washed with an aqueous sodium bicarbonate solution and water
  7. customdried
  8. concentrationconcentrated
  9. customto remove solvent
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroformethyl acetate=12:1)
  11. customcrystallized with hexane

Sources & evidence

ORD record
ord-7f80ce0f82a0473fb86b80478dcee456
Source dataset
uspto-grants-1993_04
Patent number
US05202312

Reaction notes

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