Potassium Carbonate → Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-(4-cyanophenoxy)propionate

HRID 1860081Notes

Reaction equation

HRID 1860081 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)#[N:2].CS(O[CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[C:34]([O:33][C:32]([NH:31][CH2:30][CH2:29][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:23][CH:22]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:20][CH:19]=1)=[O:38])([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 18625868Ethyl 2-(4-cyanophenoxy)-3-(4-hydroxyphenyl)propionateHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Product 1

HCID 18625774Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-(4-cyanophenoxy)propionateYield 57.3%

Procedure

In a similar manner to that described in Reference example 25, a reaction was carried out using ethyl 2-(4-cyanophenoxy)-3-(4-hydroxyphenyl)propionate (293 mg), t-butyl 2-methanesulfonyloxyethylcarbamate (560 mg) and potassium carbonate (520 mg) and the reaction mixture was treated to afford the title compound (245 mg) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-16ba483dccca4ca5a71c7d3e254b8c5b
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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