Methyl bromoacetate → HCID 14402229, compound

HRID 1382183Notes

Reaction equation

HRID 1382183 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH2:7]([NH:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)[CH3:8].C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:9]([CH2:7][CH3:8])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 5789913-Ethylaminophenol

Product 1

HCID 14402229HCID 14402229, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl bromoacetate (10.7 g, 70 mmole), 3-(ethylamino) phenol from above (4.8 g, 35 mmole), and ethyl diisopropyl amine (4.45 g, 35 mmole) were combined in 25 ml of toluene. The mixture was heated at 100° C. for 30 min. and then evaporated under vacuum and chromatographed on a silica gel column using 5% (v/v) methanol/methylene chloride. The combined fractions were washed with saturated sodium bicarbonate and neutralized with 0.1N HCL. The combined fractions were dried over Na2SO4 and evaporated to give 7.24 g of N-ethyl-N-3-hydroxyphenyl glycine methyl ester.

Workup

  1. customevaporated under vacuum
  2. customchromatographed on a silica gel column
  3. washThe combined fractions were washed with saturated sodium bicarbonate and neutralized with 0.1N HCL
  4. dry with materialThe combined fractions were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ccf382539ac54e4c9c90bea6fd1e7c0a
Source dataset
uspto-grants-1989_02
Patent number
US04806488

Reaction notes

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