Dichloromethane → HCID 131731095, compound
Reaction equation
[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]1Participants
Procedure
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.
Workup
- concentrationThe solution was concentrated under reduced pressure
- additionK2CO3 was added (1.2 g)
- waitAfter 1 hour at room temperature
- concentrationthe mixture was concentrated to dryness
- customThe final crude was purified by SiO2 chromatography (eluted with EtOAc/Hexanes: 4/1)
Sources & evidence
- ORD record
- ord-c69453c0a99e403a82468de16455a3fe
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609682B2
Reaction notes
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