Dicyclohexylcarbodiimide → 2,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid

HRID 989951

Reaktionsgleichung

Reaktionsgleichung von HRID 989951
COC1C=CC(C[O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=CC=1.[C:17]([NH:27][C@@H:28]([C:32]([OH:34])=[O:33])[CH:29]([CH3:31])[CH3:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:11][C:10]([CH3:13])([CH2:12][O:33][C:32](=[O:34])[C@@H:28]([CH:29]([CH3:30])[CH3:31])[NH:27][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:9]([OH:14])=[O:8]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 5780012,2-Dimethylpropionic acid, 4-methoxybenzyl esterHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

Produkt 1

HCID 233874902,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2,2-dimethyl propionic acid 4methoxybenzyl ester (4.7 g, 20 mmole) and N-CBz-D-valine (5.5 g, 22 mmole) in dichloromethane (100 ml) were added 4-dimethyaminopyridine (305 mg, 2.5 mmole) and DCC (5.15 g, 25 mmole). After 18 hr, the solution was washed successively with sodium bicarbonate aqueous solution, citric acid solution and water. The organic phase was dried and the residue was dissolved in dichloromethane (100 ml). To the solution was added trifluoroacetic acid (10 ml). After 3 hr, it was evaporated and the product was isolated with silica gel column chromatography. 4.5 g. The compound may be activated and esterified to a drug or further modified as described below.

Aufarbeitung

  1. washthe solution was washed successively with sodium bicarbonate aqueous solution, citric acid solution and water
  2. customThe organic phase was dried
  3. dissolutionthe residue was dissolved in dichloromethane (100 ml)
  4. additionTo the solution was added trifluoroacetic acid (10 ml)
  5. waitAfter 3 hr
  6. customit was evaporated
  7. customthe product was isolated with silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bddafb0ffba743bca7524df11985465c
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458772B1

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