Di-tert-butyl dicarbonate → 2-Methyl-2-(3-methylaminomethyl-phenoxy)-propionic acid ethyl ester

HRID 1242376Notes

Reaction equation

HRID 1242376 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[C:18](OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)([O-])O.[Na+]>O1CCOCC1.O>[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:7])([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH3:18])[CH:10]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 580095732-(3-Aminomethyl-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 670722732-Methyl-2-(3-methylaminomethyl-phenoxy)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to the procedures described in example 5D], 5E] and 5F], 2-(3-aminomethyl-phenoxy)-2-methyl-propionic acid ethyl ester was converted into the corresponding tert-butoxycarbonylamino derivative by treatment with di-tert-butyl dicarbonate and sodium hydrogen carbonate in dioxane/water at r.t., methylated at N and deprotected again to yield the title compound as a yellow oil.

Sources & evidence

ORD record
ord-ff82aaedb2a14172b8c9c777fda98549
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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