1,1'-Carbonyldiimidazole → Ethyl 3-[4-[2-(4'-methoxymethoxy-3',5'-dimethylbiphenyl-4-carbonylamino)ethoxy]phenyl]-2-phenoxypropionate

HRID 1860034Notes

Reaction equation

HRID 1860034 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.[CH3:25][O:26][CH2:27][O:28][C:29]1[C:34]([CH3:35])=[CH:33][C:32]([C:36]2[CH:41]=[CH:40][C:39]([C:42](O)=[O:43])=[CH:38][CH:37]=2)=[CH:31][C:30]=1[CH3:45].C(N1C=CN=C1)(N1C=CN=C1)=O>>[CH3:25][O:26][CH2:27][O:28][C:29]1[C:34]([CH3:35])=[CH:33][C:32]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([NH:1][CH2:2][CH2:3][O:4][C:5]3[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([O:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=3)=[O:43])=[CH:38][CH:37]=2)=[CH:31][C:30]=1[CH3:45]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 186257084'-Methoxymethoxy-3',5'-dimethylbiphenyl-4-carboxylic acidHCID 18625723Ethyl 3-[4-(2-aminoethoxy)phenyl]-2-phenoxypropionate

Product 1

HCID 18625980Ethyl 3-[4-[2-(4'-methoxymethoxy-3',5'-dimethylbiphenyl-4-carbonylamino)ethoxy]phenyl]-2-phenoxypropionateYield 23%

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 (2.07 g), which is the product of Reference example 4, 4′-methoxymethoxy-3′,5′-dimethylbiphenyl-4-carboxylic acid (1.50 g), which is the product of reference example 17(b), and carbonyldiimidazole (1.10 g) and the reaction mixture was treated to afford the desired compound (720 mg) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-5cf7e1eb5fa64961ae8906c8c766c609
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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