Tributyltin azide → N-Carboethoxy-N-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-(L)-valine benzyl ester

HRID 1609204Notes

Reaction equation

HRID 1609204 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[C@H:10]([CH:32]([CH3:34])[CH3:33])[N:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn]([N:49]=[N+:50]=[N-:51])(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1>[CH2:1]([O:8][C:9](=[O:35])[C@H:10]([CH:32]([CH3:34])[CH3:33])[N:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[NH:51][N:50]=[N:49][N:26]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 54551475N-Carboethoxy-N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester

Product 1

HCID 178473472N-Carboethoxy-N-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-(L)-valine benzyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10.0 g of N-carboethoxy-N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester and 9.2 g of tributyltin azide in 150 ml of xylene are heated to reflux for 18 hours. The reaction mixture is concentrated and the residue is stirred in 5M etherial hydrochloric acid for 15 minutes. The mixture is concentrated again, and the residue is dissolved in ether and extracted with cold 4M potassium hydroxide solution. The aqueous phase is rendered acidic and extracted with ethyl acetate. This ethyl acetate phase is washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by means of flash chromatography (250 g of silica gel, eluent N6). Amorphous product, TLC (system N6) Rf : 0.22.

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationThe reaction mixture is concentrated
  3. concentrationThe mixture is concentrated again
  4. dissolutionthe residue is dissolved in ether
  5. extractionextracted with cold 4M potassium hydroxide solution
  6. extractionextracted with ethyl acetate
  7. washThis ethyl acetate phase is washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe crude product is purified by means of flash chromatography (250 g of silica gel, eluent N6)

Sources & evidence

ORD record
ord-92f9f5c3523448699c0118bff6422e5f
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

Loading…