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

HRID 1860064Notes

Reaction equation

HRID 1860064 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([O:9][CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS(O[CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[C:36]([O:35][C:34]([NH:33][CH2:32][CH2:31][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH:10]([O:9][C:8]2[CH:24]=[CH:25][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:22][CH:21]=1)=[O:40])([CH3:39])([CH3:38])[CH3:37]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 18625938Ethyl 2-(4-t-butylphenoxy)-3-(4-hydroxyphenyl)propionateHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Product 1

HCID 18625727Ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-(4-t-butylphenoxy)propionateYield 93.1%

Procedure

In a similar manner to that described in Reference example 25, a reaction was carried out using ethyl 2-(4-t-butylphenoxy)-3-(4-hydroxyphenyl)propionate (2.37 g), which is the product of Reference example 36(b), t-butyl 2-methanesulfonyloxyethylcarbamate (3.60 g) and potassium carbonate (4.78 g) and the reaction mixture was treated to afford the title compound (3.13 g) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-5df65490277745dab4b78f2e6d45d5f8
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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