Progesterone → 4-(Aminomethyl)-2,6-dimethoxyphenol

HRID 1742441

Reaktionsgleichung

Reaktionsgleichung von HRID 1742441
CC([C@@H]1[C@@]2(C)CC[C@@H]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])CC[C@H]3[C@@H]2CC1)=O.CN1C[CH2:29][O:28]CC1.C(O[C:36](Cl)=[O:37])C(C)C.C1C2C(=[NH+:44]C3C(C=2)=CC=CC=3)C=CC=1>CN(C=O)C.C(=O)=O.C(Cl)(Cl)(Cl)Cl.CS(C)=O>[CH3:36][O:37][C:16]1[CH:15]=[C:21]([CH2:22][NH2:44])[CH:20]=[C:19]([O:28][CH3:29])[C:17]=1[OH:18]

Komponenten

8

Edukt 4

HCID 5994ProgesteroneHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 10154321HCID 10154321, Verbindung

Produkt 1

HCID 137804874-(Aminomethyl)-2,6-dimethoxyphenolAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 86602444Carbontetrachloride dry-iceLösungsmittel

Versuchsvorschrift

Progesterone hemisuccinate (90 mg, 0.209 mmole) and N-methylmorpholine (22 μl, 209 mmole) were dissolved in anhydrous DMF (2 ml). The solution was chilled in dry ice/CCl4 bath and isobutylchloroformate (30 μl, 0.229 mmole) was added. After 2 minutes a solution of the acridinium (42) (101 mg, 0.143 mmole) in dimethylsulfoxide (2 ml) containing N-methylmorpholine (3.14 μl, 0.28 mmole) was added. Stirring was continued at -20° C. for 10 minutes and the cooling bath was removed. After stirring at room temperature for 7 hours, 3 drops of water were added. The solvents were removed in vacuo and ethyl acetate was added to the residue. The oily precipitate was washed repeatedly with ethyl acetate. Upon trituration with acetonitrile (2 ml) the oil separated as solids. The product was purified on HPLC using C18Dynamax semi-prep column (10 mm×250 mm) (commercially available from Rainin Instrument Co., Inc., Woburn, Mass.) using CH3CN/H2O (0.1% trifluoroacetic acid), 55/45 as mobile phase at a flow rate of 2.75 ml/min. The peak appearing at retention time of 6.00 minutes was collected. Evaporation of solvents gave the conjugate (43) (yield=30%). MS: FAB, thioglycerol matrix, 895 (M+, without any counterions).

Aufarbeitung

  1. additionwas added
  2. customthe cooling bath was removed
  3. stirringAfter stirring at room temperature for 7 hours
  4. addition3 drops of water were added
  5. customThe solvents were removed in vacuo and ethyl acetate
  6. additionwas added to the residue
  7. washThe oily precipitate was washed repeatedly with ethyl acetate
  8. customUpon trituration with acetonitrile (2 ml) the oil separated as solids
  9. customThe product was purified on HPLC
  10. customwas collected
  11. customEvaporation of solvents

Quellen und Nachweise

ORD-Eintrag
ord-a236bfe46fb244ccb8e9b577defdced8
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05338847

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