Prednisone → 4-(1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-yloxy)-4-oxobutanoic acid

HRID 1045267

Reaktionsgleichung

Reaktionsgleichung von HRID 1045267
C[CH2:2][N:3]([CH2:6]C)[CH2:4]C.CN(C)[CH2:10][CH:11](OCCCCCCCC/C=C\C/C=C\CCCCC)[CH2:12][O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C[C@@]12[C@@:84](O)([C:85]([CH2:87][OH:88])=O)[CH2:83][CH2:82][C@H:81]1[C@@H:80]1[CH2:90][CH2:91][C:92]3[C@@:98](C)([C@H:79]1[C:77](=O)[CH2:76]2)[CH:97]=[CH:96][C:94](=O)[CH:93]=3>ClCCl>[CH3:2][N:3]([CH3:6])[CH2:4][CH:12]([O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:10][O:88][CH2:87][CH2:85][CH2:84][CH2:83][CH2:82][CH2:81][CH2:80][CH2:90]/[CH:91]=[CH:92]\[CH2:93]/[CH:94]=[CH:96]\[CH2:97][CH2:98][CH2:79][CH2:77][CH3:76]

Komponenten

6

Edukt 4

HCID 5865PrednisoneHCID 8471TriethylamineHCID 2724699PyBOPHCID 583322974-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid

Produkt 1

HCID 583322924-(1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-yloxy)-4-oxobutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

NEt3 (100 μL, 0.74 mmol, 1.0 equiv) was added dropwise to a dry dichloromethane solution (10 mL) of 4-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid and the resultant was stirred for 15 minutes under argon at room temperature. PyBOP (0.48 g, 0.93 mmol, 1.25 equiv) was added in one portion and the resultant was stirred for 10 minutes. Prednisone (0.32 g, 0.89 mmol, 1.2 equiv) was added to the mixture and the resultant was stirred at room temperature for 18 hours and then concentrated to provide a thick yellow oil, (90% pure). Purification by flash column chromatography (5-15% MeOH in chloroform and (0-15% MeOH in EtOAc) provided the desired product

Aufarbeitung

  1. stirringthe resultant was stirred for 10 minutes
  2. stirringthe resultant was stirred at room temperature for 18 hours
  3. concentrationconcentrated
  4. customto provide a thick yellow oil, (90% pure)
  5. customPurification by flash column chromatography (5-15% MeOH in chloroform and (0-15% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d53c6fdfe645492fb31e6183a179c7de
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08568772B2

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