1,1'-Carbonyldiimidazole → Ethyl 2-butyl-3-[4-[2-(3'-dimethoxymethylbiphenyl-4-carbonylamino)ethoxy]phenyl]propionate

HRID 1860014Notes

Reaction equation

HRID 1860014 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH2:18][CH2:19][CH2:20][CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.COC[C:25]1[C:30]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][O:38][CH3:39])[CH:32]=2)=[CH:29][CH:28]=[C:27]([C:40]([OH:42])=O)[CH:26]=1.[C:43](N1C=CN=C1)(N1C=CN=C1)=[O:44]>>[CH2:18]([CH:12]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:1][C:40]([C:27]2[CH:26]=[CH:25][C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([O:38][CH3:39])[O:44][CH3:43])[CH:32]=3)=[CH:29][CH:28]=2)=[O:42])=[CH:6][CH:7]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 18625891Ethyl 3-[4-(2-aminoethoxy)phenyl]-2-butylpropionateHCID 698762426, 3'-Dimethoxymethylbiphenyl-4-carboxylic acid

Product 1

HCID 18625724Ethyl 2-butyl-3-[4-[2-(3'-dimethoxymethylbiphenyl-4-carbonylamino)ethoxy]phenyl]propionateYield 98.7%

Procedure

In a similar manner to that described in Example 5, a reaction was carried out using ethyl 3-[4-(2-aminoethoxy)phenyl]-2-butylpropionate (1.55 g), which is the product of Reference example 6, 3′-dimethoxymethylbiphenyl-4-carboxylic acid (1.44 g), which is the product of reference example 14(c), and carbonyldiimidazole (1.03 g) and the reaction mixture was treated to afford the desired compound (2.72 g) as a syrup.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-292fa11afffd4b6c970c5614515041f7
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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