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1,1'-Carbonyldiimidazole → (2r)-6-Hydroxy-2,5,7,8-tetramethyl-n-[(3s)-2-oxotetrahydro-3-furanyl]-3,4-dihydro-2h-chromene-2-carboxamide

HRID 352327
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 352327
[CH3:1][C:2]1[C:3]([CH3:18])=[C:4]2[O:13][C@:12]([C:15]([OH:17])=O)([CH3:14])[CH2:11][CH2:10][C:5]2=[C:6]([CH3:9])[C:7]=1[OH:8].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:32][C@H:33]1[CH2:38][CH2:37][O:36][C:34]1=[O:35].C(N(CC)C(C)C)(C)C>C1COCC1.CN(C=O)C>[OH:8][C:7]1[C:6]([CH3:9])=[C:5]2[C:4](=[C:3]([CH3:18])[C:2]=1[CH3:1])[O:13][C@@:12]([CH3:14])([C:15]([NH:32][C@H:33]1[CH2:38][CH2:37][O:36][C:34]1=[O:35])=[O:17])[CH2:11][CH2:10]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27336672(3H)-Furanone, 3-aminodihydro-, hydrochloride (1:1), (3S)-HCID 65413546-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid, (+)-

Produkt 1

HCID 15521465(2r)-6-Hydroxy-2,5,7,8-tetramethyl-n-[(3s)-2-oxotetrahydro-3-furanyl]-3,4-dihydro-2h-chromene-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A solution of 1.82 g (7.27 mmoles) of (R)-Trolox and 1.18 g (7.27 mmoles) of 1,1′-carbonyldiimidazole (CDI) in 15 ml of anhydrous THF is stirred for 1 hour at 23° C., before adding a solution of 1 g (7.27 mmoles) of (S)-2-amino4-butyrolactone hydrochloride and 1.27 ml (7.27 mmoles) of N,N-diisopropylethylamine (DIEA) in 15 ml of anhydrous DMF. The reaction mixture is stirred for 15 hours at 23° C. and finally concentrated to dryness under vacuum. The residue is dissolved in 100 ml of AcOEt and the organic solution is washed successively with 50 ml of 1N aqueous HCl, 50 ml of H2O, 50 ml of a saturated aqueous solution of NaHCO3, 50 ml of H2O and finally 50 ml of salt water. After drying over MgSO4, the organic solution is filtered and concentrated to dryness under vacuum. The residue is taken up in 50 ml of Et2O, followed by agitating and filtering. After rinsing with 2×25 ml of Et2O, the white powder, obtained is dried under vacuum. Melting point: 195-196° C.

Aufarbeitung

  1. concentrationfinally concentrated to dryness under vacuum
  2. dissolutionThe residue is dissolved in 100 ml of AcOEt
  3. washthe organic solution is washed successively with 50 ml of 1N aqueous HCl, 50 ml of H2O, 50 ml of a saturated aqueous solution of NaHCO3, 50 ml of H2O and finally 50 ml of salt water
  4. dry with materialAfter drying over MgSO4
  5. filtrationthe organic solution is filtered
  6. concentrationconcentrated to dryness under vacuum
  7. stirringby agitating
  8. filtrationfiltering
  9. washAfter rinsing with 2×25 ml of Et2O
  10. customthe white powder, obtained
  11. customis dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0f28cd1fb4ed4c7bbba56e980a1884a0
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06747024B1

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