Triethylamine → N-[2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl-L-leucinal semicarbazone

HRID 1607416Notes

Reaction equation

HRID 1607416 reaction equation
[C:1]1([CH2:11][CH:12]([CH2:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[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.[NH2:28][C@H:29]([C:36]([NH:38][C@H:39]([CH:44]=[N:45][NH:46][C:47]([NH2:49])=[O:48])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[C:1]1([CH2:11][CH:12]([CH2:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]([NH:28][C@H:29]([C:36]([NH:38][C@H:39]([CH:44]=[N:45][NH:46][C:47]([NH2:49])=[O:48])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:30][C:31]2[N:35]=[CH:34][NH:33][CH:32]=2)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 13746611HCID 13746611, compoundHCID 178445905HCID 178445905, compound

Product 1

HCID 178445902N-[2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl-L-leucinal semicarbazone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 221 mg of (±)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionic acid and 400 mg of bis-(p-toluenesulfonic acid) salt of L-histidyl-L-leucinal semicarbazone in 5 ml of dry N,N-dimethylformamide were successively added dropwise 202 mg of diphenylphosphoryl azide and 0.28 ml of triethylamine under ice-cooling, and then the mixture was stirred for 15 hours. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1 by volume) to obtain 71 mg of N-[2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl-L-leucinal semicarbazone (isomer A) and 166 mg of isomer B.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona 5% aqueous sodium bicarbonate solution was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1 by volume)

Sources & evidence

ORD record
ord-87081bff1589437d9c5f08fcfe1d74f8
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

Loading…