Dicyclohexylcarbodiimide → HCID 86598603, Verbindung

HRID 968528

Reaktionsgleichung

Reaktionsgleichung von HRID 968528
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][C@H:11]2[C:16]([OH:18])=[O:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:20][C:21]1[N:26]=[C:25]([CH2:27][CH2:28][CH2:29]O)[CH:24]=[CH:23][CH:22]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:20][C:21]1[N:26]=[C:25]([CH2:27][CH2:28][CH2:29][O:17][C:16]([C@@H:11]2[CH2:12][S:13][CH2:14][CH2:15][N:10]2[S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=2)(=[O:9])=[O:8])=[O:18])[CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 1091326-Methyl-2-pyridylpropan-1-olHCID 69415969(3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid

Produkt 1

HCID 86598603HCID 86598603, VerbindungAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.301 g (1 mmol) of (3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid, 0.230 g (1.5 mmol) of 3-(6-methyl-pyridin-2-yl)-propanol, 0.088 g (0.33 mmol) of CAS, 0.227 g (1.2 mmol) of DCC and 0.04 g (0.33 mmol) of DMAP were dissolved in 15 mL of CH2Cl2. The mixture was stirred for 24 h at room temperature. The solid was filtrated and the solvent was evaporated. The residual was dissolved in a suitable amount of ethyl acetate (20 ml) and then the mixture was filtered to remove insoluble substance. The ethyl acetate was added to 60 ml and then the liquid was washed with 10% NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. After the drying agent was removed and part of ethyl acetate was evaporated, the crude product was purified by flash column chromatography (eluent: ethyl acetate:cyclohexane=1:1) to obtain the product as a oil (0.23 g).

Aufarbeitung

  1. filtrationThe solid was filtrated
  2. customthe solvent was evaporated
  3. dissolutionThe residual was dissolved in a suitable amount of ethyl acetate (20 ml)
  4. filtrationthe mixture was filtered
  5. customto remove insoluble substance
  6. additionThe ethyl acetate was added to 60 ml
  7. washthe liquid was washed with 10% NaHCO3 solution, saturated NaCl solution
  8. dry with materialdried over Na2SO4
  9. customAfter the drying agent was removed
  10. custompart of ethyl acetate was evaporated
  11. customthe crude product was purified by flash column chromatography (eluent: ethyl acetate:cyclohexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3e30d5d767934466873447b643eb1fab
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304057B2

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