Triethylamine → HCID 59253981, compound

HRID 501865

Reaction equation

HRID 501865 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH2:25]([O:32][CH2:33][C:34](Cl)=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:34](=[O:35])[CH2:33][O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

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

Product 1

HCID 59253981HCID 59253981, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 6-(4-aminophenoxy)-hexanoic acid methyl ester 17 (25 g, 105 mmol) and triethylamine (21.4 g, 211.6 mmol) in acetone (200 ml) at 0° C. was added dropwise benzyloxy acetyl chloride (25 g, 135.5 mmol) followed by stirring at room temp. for 12 hrs. The solids were filtered off, acetone distilled off and water (100 ml) added. Crude 53 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), then water (100 ml), dried over sodium sulphate and distilled. Crude 53 was purified by column chromatography on silica gel using benzene as eluant to get pure 53 (9 g, 22.2%), an off-white powder with a m.p. between 46-49° C.

Workup

  1. filtrationThe solids were filtered off
  2. distillationacetone distilled off
  3. additionwater (100 ml) added
  4. extractionCrude 53 was extracted into chloroform
  5. washwashed with 5% sodium bicarbonate solution (2×100 ml)
  6. dry with materialwater (100 ml), dried over sodium sulphate
  7. distillationdistilled
  8. customCrude 53 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b6e58a072fec47b98761066fa012a2fa
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Linked notes

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