Diisopropylethylamine → 4-methoxycarbonyl-4-methyl-pentanoic acid N-butyl-N-(2'-cyano-biphenyl-4-ylmethyl)-amide

HRID 2380673Notes

Reaction equation

HRID 2380673 reaction equation
[CH3:1][O:2][C:3]([C:5]([CH3:12])([CH3:11])[CH2:6][CH2:7][C:8](Cl)=[O:9])=[O:4].[CH2:13]([NH:17][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][CH:20]=1)[CH2:14][CH2:15][CH3:16].CCN(C(C)C)C(C)C>C(OCC)(=O)C>[CH2:13]([N:17]([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][CH:20]=1)[C:8](=[O:9])[CH2:7][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:12])[CH3:11])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 14980523Methyl 5-chloro-2,2-dimethyl-5-oxopentanoateHCID 153383534'-Butylaminomethyl-2-cyanobiphenyl

Product 1

HCID 537457074-methoxycarbonyl-4-methyl-pentanoic acid N-butyl-N-(2'-cyano-biphenyl-4-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The starting material can be prepared, for example, as follows: A solution of 3.3 g (17 mmol) of 4-methoxycarbonyl-4-methyl-pentanoic acid chloride in 20 ml of ethyl acetate is added dropwise at from 0° to 5° to a solution of 3.0 g (11.3 mmol) of N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amine and 6.5 ml of Hunig base in 50 ml of ethyl acetate. The reaction mixture is stirred for 1 hour and then worked up analogously to Example 1 b) to yield 4-methoxycarbonyl-4-methyl-pentanoic acid N-butyl-N-(2'-cyano-biphenyl-4-ylmethyl)-amide in the form of an oil that has an Rf value of 0.27 [toluene/methanol (19:1)] and is further used in crude form.

Sources & evidence

ORD record
ord-e7c0ccc924ea4979adbbfb6c59490495
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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