Dicyclohexylcarbodiimide → 4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

HRID 1098732Notes

Reaction equation

HRID 1098732 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[CH2:14]([O:21][CH2:22][C:23](O)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:23](=[O:24])[CH2:22][O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 290301(Benzyloxy)acetic acidHCID 6422115Methyl(4-aminophenoxy)acetate

Product 1

HCID 592539834-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl esterYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (4-aminophenoxy)-acetic acid methyl ester 3 (20 g, 110.5 mmol) and benzyloxy acetic acid (20.4 g, 123 mmol) in anhydrous dichloromethane (200 ml) under nitrogen atmosphere was added dropwise a solution of 1,3-dicyclohexyl carbo-diimide (63.2 g, 306 mmol) in anhydrous dichloromethane (80 ml) then stirred at room temp. for 12 hours. The solids were filtered off, the dichloromethane was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml) added, and the solids dried over sodium sulphate and distilled to get crude 49. Crude 49 was purified by column chromatography on silica gel using benzene as eluant to get pure 49 (25 g, 68.9%) as a white powder with an m.p. between 76-77.5° C.

Workup

  1. filtrationThe solids were filtered off
  2. washthe dichloromethane was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml)
  3. additionadded
  4. dry with materialthe solids dried over sodium sulphate
  5. distillationdistilled
  6. customto get crude 49
  7. customCrude 49 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-da38bfc7f6f7420d8598b29e57f8a0a2
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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