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Triethylamine → 4-methoxycarbonyl-4-methyl-pentanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide

HRID 2380677
Notes
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Reaction equation

HRID 2380677 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].[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=1)#[N:14].C(N(CC)CC)C>C(Cl)Cl>[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[CH:23][C:24]([CH2:27][N:28]([CH2:29][CH2:30][CH3:31])[C:8](=[O:9])[CH2:7][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:12])[CH3:11])=[CH:25][CH:26]=1)#[N:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14980523Methyl 5-chloro-2,2-dimethyl-5-oxopentanoateHCID 15338355N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine

Product 1

HCID 538386644-methoxycarbonyl-4-methyl-pentanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting material can be prepared, for example, as follows: 2.89 g of 4-methoxycarbonyl-4-methyl-pentanoic acid chloride are added to a solution of 2.50 g of N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine and 2.09 ml of triethylamine in 100 ml of CH2Cl2, and the mixture is stirred for 1 hour. The reaction mixture is washed twice with 50 ml of water each time and the combined aqueous phases are extracted with 50 ml of CH2Cl2. The crude product obtained from the organic phase by the customary procedure is purified by chromatography on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (98:2) as eluant to yield pure 4-methoxycarbonyl-4-methyl-pentanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide that has an Rf value of 0.56 [CH2Cl2 /CH3OH (95:5)].

Workup

  1. washThe reaction mixture is washed twice with 50 ml of water each time
  2. extractionthe combined aqueous phases are extracted with 50 ml of CH2Cl2
  3. customThe crude product obtained from the organic phase by the customary procedure
  4. customis purified by chromatography on silica gel 60 (40-63 μm)

Sources & evidence

ORD record
ord-91587b9ce4e6426a87ba72a1d3d4abf9
Source dataset
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05369110

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes