Water → N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-phenyl}-oxamic acid ethyl ester

HRID 1607158Notes

Reaction equation

HRID 1607158 reaction equation
B(Br)(Br)Br.[CH2:5]([O:7][C:8](=[O:37])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([O:32]C)[C:24]=2[CH2:34][CH2:35][CH3:36])[CH:13]=1)=[O:10])[CH3:6].O>C(Cl)Cl>[CH2:5]([O:7][C:8](=[O:37])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=2[CH2:34][CH2:35][CH3:36])[CH:13]=1)=[O:10])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 54035976HCID 54035976, compound

Product 1

HCID 44269726N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-phenyl}-oxamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the course of 5 minutes 3.0 g of boron tribromide are added dropwise to a solution, cooled to -78° C., of 2.2 g of N-{3-[3-(4-acetyl-3-methoxy-2-n-propylphenoxy)-propoxy]-phenyl}-oxamic acid ethyl ester in 20 ml of methylene chloride. The whole is then stirred for 6 hours at room temperature. While cooling, 5 ml of water are added and the organic phase is separated off and concentrated by evaporation under reduced pressure. After recrystallisation from methylene chloride/ether there is obtained N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-phenyl}-oxamic acid ethyl ester, which can be characterised by hydrolysis to form the free acid having a melting point of 159°-160°.

Workup

  1. temperatureWhile cooling
  2. customthe organic phase is separated off
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customAfter recrystallisation from methylene chloride/ether there

Sources & evidence

ORD record
ord-96502c84bf804b9bb6ff5546f57ca381
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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