Triethylamine → HCID 178501404, compound

HRID 986357Notes

Reaction equation

HRID 986357 reaction equation
[C:1]1([CH2:11][CH:12]([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:18])[C:13](O)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH3:27][O:28][C:29](=[O:38])[C@H:30]([CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)[NH2:31].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:27][O:28][C:29](=[O:38])[C@H:30]([CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)[NH:31][C:13](=[O:14])[CH:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 139139432-(1-Naphthylmethyl)-3-morpholinocarbonylpropionic acidHCID 178419105HCID 178419105, compound

Product 1

HCID 178501404HCID 178501404, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.89 g of 2-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionic acid and 0.79 g of L-histidine methyl ester dihydrochloride in 23 ml of N,N-dimethylformamide were added 0.70 ml of diphenylphosphoryl azide and 1.50 ml of triethylamine with stirring under ice-cooling, and then the mixture was additionaly stirred for 16 hours. The reaction mixture was evaporated under reduced pressure, and to the residue was added a 5% aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. To the residue was added diethyl ether, and the precipitate was collected by filtration to obtain 1.25 g of N-[2-(1-naphthylmethyl)-3 -(morpholinocarbonyl)propionyl]-L-histidine methyl ester as a white powder. To a soluiton of 0.98 g of the ester compound in 10 ml of methanol was added 0.52 g of hydrazide monohydrate, and then the mixture was stirred for 4 hours. The reaction mixture was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1 by volume) to obtain 0.23 g of N-[2-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-L-histidine hydrazide having an Rf1 value of 0.49 as a white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was additionaly stirred for 16 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additionto the residue was added a 5% aqueous sodium bicarbonate solution
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. additionTo the residue was added diethyl ether
  10. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c53d525b971e4300b15bd7be2c6afc12
Source dataset
uspto-grants-1987_12
Patent number
US04711958

Reaction notes

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