Triethylamine → 6-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester

HRID 2169746Notes

Reaction equation

HRID 2169746 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:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1.C(N(CC)CC)C>CC(C)=O>[CH3:13][O:14][C:15](=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][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:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester

Product 1

HCID 592539816-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl esterYield 22.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyloxyacetyl chloride (25 gm, 135.5 mmol) was added dropwise to a mixture of 6-(4-aminophenoxy)hexanoic acid methyl ester 21 (25 g, 105 mmol) and triethylamine (21.4 g, 211.6 mmol) in acetone (200 ml) at 0° C. and stirred at room temp. for 12 hrs. Solids were filtered off, acetone distilled off and water (100 ml) added. Crude 70 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml), dried over sodium sulphate and distilled. Crude 70 was purified by column chromatography on silica gel using benzene as eluant to get pure 70 (9 g, 22.2%) as a off-white powder. M.p: 46-49° C.

Workup

  1. filtrationSolids were filtered off
  2. distillationacetone distilled off
  3. additionwater (100 ml) added
  4. extractionCrude 70 was extracted into chloroform
  5. washwashed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml)
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled
  8. customCrude 70 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f379199dbce44f76b9bedcb67f2d1822
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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