Ethyl chloroformate → Ethyl 2-{{4-{2-[2-(3-methoxyphenoxy)-2-methylpropionylamino]-ethyl}-phenoxy}}-2-methylpropionate

HRID 26796Notes

Reaction equation

HRID 26796 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=O.[NH2:16][CH2:17][CH2:18][C:19]1[CH:33]=[CH:32][C:22]([O:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1.ClC(OCC)=O>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C:7]([CH3:12])([CH3:11])[C:8]([NH:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:23][C:24]([CH3:30])([CH3:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:32][CH:33]=1)=[O:10]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 37816632-(3-Methoxyphenoxy)-2-methylpropanoic acidHCID 19356632Ethyl 2-[4-(2-aminoethyl)-phenoxy]-2-methylpropionate

Product 1

HCID 21322713Ethyl 2-{{4-{2-[2-(3-methoxyphenoxy)-2-methylpropionylamino]-ethyl}-phenoxy}}-2-methylpropionateYield 84%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner analogous to that described in Example 4, from 2-(3-methoxyphenoxy)-2-methylpropionic acid and ethyl 2-[4-(2-aminoethyl)-phenoxy]-2-methylpropionate, in the presence of triethylamine and ethyl chloroformate, there is obtained, in a yield of 84% of theory, ethyl 2-{{4-{2-[2-(3-methoxyphenoxy)-2-methylpropionylamino]-ethyl}-phenoxy}}-2-methylpropionate which, after recrystallization from cyclohexane and ethyl acetate, melts at 68°-69° C. and from this 2-{{4-{2-[2-(3-methoxyphenoxy)-2-methylpropionylamino]-ethyl}-phenoxy}}-2-methylpropionic acid in a yield of 64% of theory which, after recrystallization from cyclohexane and ethyl acetate, melts at 80°-81° C.

Sources & evidence

ORD record
ord-a8b6ce499f984df08f2513e2f827ea46
Source dataset
uspto-grants-1979_04
Patent number
US04151303

Reaction notes

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