Reaction equation
[O-]S(C(F)(F)F)(=O)=O.[Sn+2].[O-]S(C(F)(F)F)(=O)=O.[CH2:18]([O:21][CH2:22][CH2:23][CH:24]([NH:33][CH2:34][C@@H:35]([OH:52])[C@@H:36]([NH:44]C(=O)OC(C)(C)C)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)[CH:19]=[CH2:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:18]([O:21][CH2:22][CH2:23][CH:24]([NH:33][CH2:34][C@@H:35]([OH:52])[C@@H:36]([NH2:44])[CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)[CH:19]=[CH2:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Step R (5): Tin (II) triflate (1.2 g, 2.89 mmol) was added to a 0° C. solution of tert-butyl (2S,3R)-4-(3-(allyloxy)-1-(3-methoxyphenyl)propylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate from Step R (4) (700 mg, 1.45 mmol) in dry DCM (30 mL). The reaction was warmed to rt and stirred for 16 h. The reaction was neutralized with saturated NaHCO3 and the product was extracted with EtOAc. The organic phase was separated, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 320 mg (57% yield) of the title compound. LC-MS (M+H)+=385.42; 1H NMR (300 MHz, CDCl3) δ ppm 2.05-2.80 (m, 4H) 2.78-3.54 (m, 4H) 3.63-3.97 (m, 6H) 4.99-5.30 (m, 2H) 5.65-5.94 (m, 1H) 6.76-7.33 (m, 10H) 7.53-7.74 (m, 1H).
Workup
- extractionthe product was extracted with EtOAc
- customThe organic phase was separated
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-36f29ebd806949619056cfdeb9199309
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772221B2
Linked notes
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