Potassium Hydroxide → HCID 178448926, compound

HRID 2380670Notes

Reaction equation

HRID 2380670 reaction equation
[CH2:1]([N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:19][CH:18]=1)[C:6](=[O:15])[CH2:7][C:8]([C:11]([O:13]C)=[O:12])([CH3:10])[CH3:9])[CH2:2][CH2:3][CH3:4].C([Sn]([N:44]=[N+:45]=[N-:46])(CCCC)CCCC)CCC.[OH-].[K+]>CC1C=CC=CC=1C>[CH2:1]([N:5]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[NH:46][N:45]=[N:44][N:30]=2)=[CH:21][CH:22]=1)[C:6](=[O:15])[CH2:7][C:8]([C:11]([OH:13])=[O:12])([CH3:9])[CH3:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4984872Tributyltin azideHCID 53946869HCID 53946869, compound

Product 1

HCID 178448926HCID 178448926, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4.0 g (9.8 mmol) of 3-methoxycarbonyl-3-methyl-butanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide and 4.3 g (13 mmol) of tributyltin azide in 80 ml of o-xylene is reacted analogously to Example 1 for 24 hours. For hydrolysis, the reaction mixture is stirred with 50 ml of 2N potassium hydroxide solution at from 40 bis 50° for 4 hours. The aqueous phase is separated and acidified with 2N hydrochloric acid, and the oil which separates is extracted with ethyl acetate. Washing of the ethyl acetate solution with water, drying over MgSO4 and concentration by evaporation yield 3-carboxy-3-methyl-butanoic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amide in the form of a colourless foam that has an Rf value of 0.25 [toluene/isopropanol/glacial acetic acid (170:30:2)].

Workup

  1. customFor hydrolysis
  2. customThe aqueous phase is separated
  3. extractionthe oil which separates is extracted with ethyl acetate
  4. washWashing of the ethyl acetate solution with water
  5. dry with materialdrying over MgSO4 and concentration by evaporation

Sources & evidence

ORD record
ord-20b063e1b955492d89dc18948eb65658
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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