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

HRID 546358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546358
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-baa002df4e414ce0a421768acd481f70
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935843B2

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