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

HRID 1860009Notes

Reaction equation

HRID 1860009 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][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38](O)=[O:39])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25].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:38]([C:35]2[CH:36]=[CH:37][C:32]([C:29]3[CH:30]=[CH:31][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=3)=[CH:33][CH:34]=2)=[O:39])=[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 142508264-[4-(Methoxycarbonyl)phenyl]benzoic acidHCID 18625891Ethyl 3-[4-(2-aminoethoxy)phenyl]-2-butylpropionate

Product 1

HCID 18626044Ethyl 2-butyl-3-[4-[2-(4'-methoxycarbonylbiphenyl-4-carbonylamino)ethoxy]phenyl]propionateYield 37.8%

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 (375 mg), which is the product of Reference example 6, 4′-methoxycarbonylbiphenyl-4-carboxylic acid (328 mg) and carbonyldiimidazole (225 mg) and the reaction mixture was treated to afford the title compound (257 mg) as colorless crystals.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-645ddc704ac645fdb85fd4555a75424f
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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