P,P-Diphenylphosphinic azide → HCID 178445900, compound

HRID 1607417Notes

Reaction equation

HRID 1607417 reaction equation
[C:1]1([CH2:11][CH:12]([CH2:16][CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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.[NH2:25][C@H:26]([C:33]([NH:35][C@H:36]([CH:41]=[N:42][NH:43][C:44]([NH2:46])=[O:45])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])[CH2:27][C:28]1[N:32]=[CH:31][NH:30][CH:29]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[C:1]1([CH2:11][CH:12]([CH2:16][CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]([NH:25][C@H:26]([C:33]([NH:35][C@H:36]([CH:41]=[N:42][NH:43][C:44]([NH2:46])=[O:45])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])[CH2:27][C:28]2[N:32]=[CH:31][NH:30][CH:29]=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

7

Reactant 4

HCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 53925726(+/-)-2-(1-Naphthylmethyl)-5-phenyl-4-pentenoic acidHCID 178445905HCID 178445905, compound

Product 1

HCID 178445900HCID 178445900, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 190 mg of (±)-2-(1-naphthylmethyl)-5-phenyl-4-pentenoic acid and 400 mg of bis(P-toluenesulfonic acid) salt of L-histidyl-L-leucinal semicarbazone in 7 ml of N,N-dimethylformamide were successively added 0.16 ml of diphenylphosphoryl azide and 0.28 ml of triethylamine under ice-cooling, and the mixture was stirred overnight. To the reaction mixture was added a 5% aqueous sodium bicarbonate solution, and the mixture was extracted withh ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: chloroform/methanol=15/1 by volume) to obtain 151 mg of N-[(±)-2-(1-naphthylmethyl)-5-phenyl-4-pentenoyl]-L-histidyl-L-leucinal semicarbazone as a white powder.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted withh ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (eluent: chloroform/methanol=15/1 by volume)

Sources & evidence

ORD record
ord-c7a7a68bbcd7411991d531ef0d1bc376
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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