Triethylamine → 3,3-dimethyl-4-methoxycarbonyl-butanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide

HRID 2380676Notes

Reaction equation

HRID 2380676 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=1)#[N:9].[Cl-].[CH3:28][O:29][C:30](=[O:39])[CH2:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34]([OH:36])=O>C(Cl)Cl>[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:24][CH2:25][CH3:26])[C:34](=[O:36])[CH2:33][C:32]([CH3:38])([CH3:37])[CH2:31][C:30]([O:29][CH3:28])=[O:39])=[CH:20][CH:21]=1)#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15338355N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amineHCID 867482873,3-Dimethylglutaric acid monomethyl ester monochloride

Product 1

HCID 536371373,3-dimethyl-4-methoxycarbonyl-butanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.83 ml of triethylamine are added to a solution of 2.19 g of N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine and 2.37 g of 3,3-dimethylglutaric acid monomethyl ester monochloride in 100 ml of CH2Cl2 and the mixture is stirred at room temperature for 2 hours. Extraction twice with 50 ml of water each time and extraction of the aqueous phase with 40 ml of CH2Cl2 produces an organic phase which, after being concentrated by evaporation, yields by the customary procedure 3,3-dimethyl-4-methoxycarbonyl-butanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide that has an Rf value of 0.66 [CH2Cl2 /CH3OH (95:5)].

Workup

  1. extractionExtraction twice with 50 ml of water
  2. extractioneach time and extraction of the aqueous phase with 40 ml of CH2Cl2
  3. customproduces an organic phase which
  4. concentrationafter being concentrated by evaporation

Sources & evidence

ORD record
ord-7f19924fb62649ada6c2851fc4c9f959
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

Loading…