Dichloromethane → HCID 131731095, Verbindung

HRID 1913105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913105
[CH2:1]1[C@@H:17]([NH2:18])[C@@H:16]2[O:19][C:20]3=[C:21]([OH:24])[CH:22]=[CH:23][C:6]4=[C:7]3[C@:8]32[CH2:9][CH2:10][N:11]([CH2:12][CH:13]2[CH2:15][CH2:14]2)[C@H:4]([CH2:5]4)[C@:3]3([OH:25])[CH2:2]1.C1C=CC2C(=CC=C[C:35]=2[C:36](O)=[O:37])C=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2N=N1.CCN([CH:72]([CH3:74])[CH3:73])C(C)C.[CH2:75](Cl)Cl>>[CH:13]1([CH2:12][N:11]2[CH2:10][CH2:9][C@:8]34[C:7]5[C:20]6[O:19][C@H:16]3[C@H:17]([NH:18][C:36](=[O:37])[CH2:35][C:49]3[C:50]7[C:51](=[CH:75][CH:74]=[CH:72][CH:73]=7)[CH:52]=[CH:53][CH:54]=3)[CH2:1][CH2:2][C@@:3]4([OH:25])[C@H:4]2[CH2:5][C:6]=5[CH:23]=[CH:22][C:21]=6[OH:24])[CH2:14][CH2:15]1

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 68471-Naphthoic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5486948beta-Naltrexamine

Produkt 1

HCID 131731095HCID 131731095, Verbindung

Versuchsvorschrift

b-Naltrexamine (400 mg, 1.16 mmol), naphthoic acid (399 mg, 2.32 mmol) and BOP (1.03 g, 2.32 mmol) were dissolved in DCM (15 mL). To this solution, DIPEA (600 mL, 3.25 mmol) was added and the mixture was stirred at room temperature for 16 hours. The solution was concentrated under reduced pressure and the residue was taken up in MeOH (15 mL), and K2CO3 was added (1.2 g). After 1 hour at room temperature, the mixture was concentrated to dryness. The final crude was purified by SiO2 chromatography (eluted with EtOAc/Hexanes: 4/1) to afford the desired compound as a white solid. The target compound was recrystallized from an acetone/hexanes (1/4: v/v) mixture providing a white solid (473 mg, 82%). The title compound was then subsequently converted into the HCl salt for biological testing.

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionK2CO3 was added (1.2 g)
  3. waitAfter 1 hour at room temperature
  4. concentrationthe mixture was concentrated to dryness
  5. customThe final crude was purified by SiO2 chromatography (eluted with EtOAc/Hexanes: 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-c69453c0a99e403a82468de16455a3fe
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609682B2

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