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

HRID 1860018Notes

Reaction equation

HRID 1860018 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.[CH3:22][O:23][CH2:24][O:25][CH2:26][C:27]1[CH:28]=[C:29]([C:33]2[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[CH:35][CH:34]=2)[CH:30]=[CH:31][CH:32]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>>[CH2:18]([CH:12]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:1][C:39]([C:36]2[CH:35]=[CH:34][C:33]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][O:25][CH2:24][O:23][CH3:22])[CH:28]=3)=[CH:38][CH:37]=2)=[O:40])=[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 186260473'-Methoxymethoxymethylbiphenyl-4-carboxylic acid

Product 1

HCID 18625844Ethyl 2-butyl-3-[4-[2-(3'-methoxymethoxymethylbiphenyl-4-carbonylamino)ethoxy]phenyl]propionateYield 85.7%

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 (358 mg), which is the product of Reference example 6, 3′-methoxymethoxymethylbiphenyl-4-carboxylic acid (333 mg), which is the product of reference example 15(c), and carbonyldiimidazole (238 mg) and the reaction mixture was treated to afford the desired compound (573 mg) as a brown syrup.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-2229e622224f4420b14664e5579240c7
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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