Tributyltin azide → HCID 178447276, compound

HRID 1739084Notes

Reaction equation

HRID 1739084 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[C@H:10]([CH:34]([CH3:36])[CH3:35])[N:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]#[N:32])=[CH:21][C:20]=1[Br:33])[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn]([N:51]=[N+:52]=[N-:53])(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1>[CH2:1]([O:8][C:9](=[O:37])[C@H:10]([CH:34]([CH3:36])[CH3:35])[N:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:53][N:52]=[N:51][N:32]=2)=[CH:21][C:20]=1[Br:33])[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 54539559HCID 54539559, compound

Product 1

HCID 178447276HCID 178447276, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4.5 g (8 mmol) of N-[(3-bromo-2'-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine benzyl ester and 3.4 g (10.4 mmol) of tributyltin azide in 50 ml of xylene is heated to boiling under reflux for 20 hours. Working-up analogously to Example 54 and "flash"-chromatographic purification (toluene-methanol 4:1) gives the title compound as a colourless foam (Rf 0.57, system A2).

Workup

  1. temperatureunder reflux for 20 hours
  2. customWorking-up analogously to Example 54 and "flash"-chromatographic purification (toluene-methanol 4:1)

Sources & evidence

ORD record
ord-e7eab10fe4d445748eba36b151e10e03
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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