(1,1'-Biphenyl)-4-carboxylic acid → Ethyl 3-[4-[2-(biphenyl-4-carbonylamino)ethoxy]phenyl]-2-phenoxypropionate

HRID 1859885Notes

Reaction equation

HRID 1859885 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[CH:27][CH:26]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>>[C:25]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:26]=[CH:27][C:28]([C:31]([NH:1][CH2:2][CH2:3][O:4][C:5]2[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=2)=[O:32])=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 18625723Ethyl 3-[4-(2-aminoethoxy)phenyl]-2-phenoxypropionate

Product 1

HCID 18625735Ethyl 3-[4-[2-(biphenyl-4-carbonylamino)ethoxy]phenyl]-2-phenoxypropionateYield 27.2%

Procedure

In a similar manner to that described in Example 5, a reaction was carried out using ethyl 3-[4-(2-aminoethoxy)phenyl]-2-phenoxypropionate (666 mg), which is the product of Reference example 4, biphenyl-4-carboxylic acid (400 mg) and carbonyldiimidazole (393 mg) and the reaction mixture was treated to give the title compound (280 mg) as a white powder.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-7bc392404ab14739bd7d72dd5c97ab06
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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