Potassium Hydroxide → HCID 178448927, compound

HRID 2380667Notes

Reaction equation

HRID 2380667 reaction equation
[CH2:1]([N:5]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:17][CH:16]=1)[C:6](=[O:13])[CH2:7][CH2:8][C:9]([O:11]C)=[O:10])[CH2:2][CH2:3][CH3:4].C([Sn]([N:42]=[N+:43]=[N-:44])(CCCC)CCCC)CCC.[OH-].[K+]>CC1C=CC=CC=1C>[CH2:1]([N:5]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[NH:44][N:43]=[N:42][N:28]=2)=[CH:19][CH:20]=1)[C:6](=[O:13])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4984872Tributyltin azideHCID 540165583-methoxycarbonylpropanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

Product 1

HCID 178448927HCID 178448927, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 8.8 g (22.7 mmol) of 3-methoxycarbonylpropanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide and 9.8 g (29.5 mmol) of tributyltin azide in 100 ml of o-xylene is heated under reflux for 20 hours. The reaction mixture is then cooled to 20° and 100 ml of 1N potassium hydroxide solution are added thereto. The reaction mixture is stirred thoroughly for 2 hours, and the aqueous phase is separated and acidified with 2N hydrochloric acid. The resin which separates is extracted with ethyl acetate. The crude product, obtained by concentration of the ethyl acetate phase by evaporation, is flash-chromatographed on 500 g of silica gel [toluene/isopropanol/glacial acetic acid (170:30:2)] to yield 3-carboxypropanoic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amide in the form of a light-brown foam that has an Rf value of 0.20 [toluene/isopropanol/glacial acetic acid (170:30:2)]. ##STR8##

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureThe reaction mixture is then cooled to 20°
  3. customthe aqueous phase is separated
  4. extractionThe resin which separates is extracted with ethyl acetate
  5. customThe crude product, obtained by concentration of the ethyl acetate phase by evaporation
  6. customis flash-chromatographed on 500 g of silica gel [toluene/isopropanol/glacial acetic acid (170:30:2)]

Sources & evidence

ORD record
ord-21242f0c92f8464ca50310000e6b8dc6
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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