3-(4-Hydroxyphenyl)propionic acid → 3-(4-Hydroxy-phenyl)-2-{2-[3-(4-hydroxy-phenyl)-propionyloxy]-acetylamino}-propionic acid methyl ester

HRID 546358Notes

Reaction equation

HRID 546358 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:30])[CH:16]([NH:25][C:26](=[O:29])[CH2:27][OH:28])[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:28][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 10868DicyclohexylcarbodiimideHCID 588958052-(2-Hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Product 1

HCID 588958063-(4-Hydroxy-phenyl)-2-{2-[3-(4-hydroxy-phenyl)-propionyloxy]-acetylamino}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3(4-hydroxy phenyl) propionic acid (10 grams, 60.17 mmol) and 2-(2-hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 3 (15.2 grams, 60.07 mmol) in anhydrous dichloromethane (100 mL) under a nitrogen atmosphere at 0° C. is added dropwise to a solution of 1,3-dicyclohexyl carbodiimide (31 grams, 150.24 mmol) in dichloro methane (75 mL). The mixture 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 6, which can be purified in an 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 6, which
  6. customcan be purified in an appropriate solvent

Sources & evidence

ORD record
ord-baa002df4e414ce0a421768acd481f70
Source dataset
uspto-grants-2011_05
Patent number
US07935843B2

Reaction notes

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