Tributyltin azide → HCID 178447281, compound

HRID 1609213Notes

Reaction equation

HRID 1609213 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([N:17]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]#[N:38])=[CH:27][CH:26]=2)[C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn]([N:52]=[N+:53]=[N-:54])(CCCC)CCCC)CCC>CC1C=CC=CC=1C>[CH2:1]([O:8][C:9]([C:11]1([N:17]([C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[NH:54][N:53]=[N:52][N:38]=3)=[CH:29][CH:30]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 20083492HCID 20083492, compound

Product 1

HCID 178447281HCID 178447281, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3.3 g (6.5 mmol) of N-(1-benzyloxycarbonylcyclohexyl)-N-(2'-cyanobiphenyl-4-ylmethyl)-N-pentanoyl-amine, 4.1 g (12.3 mmol) of tributyltin azide and 30 ml of o-xylene is heated to reflux for 44 hours. Working-up of the mixture in a manner analogous to that described in Example 23 yields the N-(1-benzyloxycarbonylcyclohexyl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine in the form of light-brown crystals melting between 189° and 190° (from ethyl acetate/diethyl ether).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 44 hours

Sources & evidence

ORD record
ord-730c048f99294a87bf3a56d99e76e45f
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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