Triethylamine → 2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester

HRID 1957866Notes

Reaction equation

HRID 1957866 reaction equation
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:26])[CH:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)[CH3:17].C(N(CC)CC)C>CC(C)=O>[CH3:13][O:14][C:15](=[O:26])[CH:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:10](=[O:11])[CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 22060471Methyl 2-(4-aminophenoxy)propanoate

Product 1

HCID 592539632-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl esterYield 59.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyloxyacetyl chloride (28 g, 152 mmol) was added dropwise to a mixture of 2-(4-aminophenoxy)propionic acid methyl ester 18 (20 g, 102.5 mmol) and triethylamine (23 ml, 165 mmol) in acetone (120 ml) at 0° C. and stirred at room temperature for 12 hrs. Solids were filtered off, acetone distilled off and water (100 ml) added. Crude 68 was extracted into chloroform, washed with 5% sodium bicarbonate (2×100 ml), water (200 ml), dried over sodium sulphate and distilled. Crude 68 was purified by column chromatography on silica gel using benzene as eluant to get pure 68 (21 g, 59.8%) as a light brown powder. M.p: 67-70° C.

Workup

  1. filtrationSolids were filtered off
  2. distillationacetone distilled off
  3. additionwater (100 ml) added
  4. extractionCrude 68 was extracted into chloroform
  5. washwashed with 5% sodium bicarbonate (2×100 ml), water (200 ml)
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled
  8. customCrude 68 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ca991032d8984228b635676cd4c8fcf6
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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