Dicyclohexylcarbodiimide → 2-{2-[2-(4-Hydroxy-phenoxy)-acetoxy]-acetylamino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester

HRID 546361Notes

Reaction equation

HRID 546361 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:30])[CH:16]([NH:25][C:26](=[O:29])[CH2:27]O)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:13][O:14][C:15](=[O:30])[CH:16]([NH:25][C:26](=[O:29])[CH2:27][O:9][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][CH:11]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 15881(4-Hydroxyphenoxy)acetic acidHCID 588958052-(2-Hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Product 1

HCID 588958072-{2-[2-(4-Hydroxy-phenoxy)-acetoxy]-acetylamino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-hydroxy-phenoxy)-acetic acid 12 (10 grams, 59.52 mmol) and 2-(2-hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 3 (15 grams, 59.28 mmol) in anhydrous dichloro methane (100 mL) under an nitrogen atmosphere at 0° C. is added to a solution of 1,3-dicyclohexyl carbodiimide (31 grams, 150.24 mmol) in dichloro methane (75 mL) drop wise. Later it is stirred at room temperature for 6 hours. The solids are filtered off. The organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL), dried over sodium sulphate, and distilled to give crude 13, which can be purified in appropriate solvent.

Workup

  1. filtrationThe solids are filtered off
  2. washThe organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL)
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled
  5. customto give crude 13, which
  6. customcan be purified in appropriate solvent

Sources & evidence

ORD record
ord-098ae06b09584bebaf73a40cce664ac1
Source dataset
uspto-grants-2011_05
Patent number
US07935843B2

Reaction notes

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