Sodium Bicarbonate → (2R,3S)-1-(3-(allyloxy)-1-(3-methoxyphenyl)propylamino)-3-amino-4-phenylbutan-2-ol

HRID 501686Notes

Reaction equation

HRID 501686 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

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2776843Tin(II) trifluoromethanesulfonateHCID 86622322tert-butyl (2S,3R)-4-(3-(allyloxy)-1-(3-methoxyphenyl)propylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Product 1

HCID 59423687(2R,3S)-1-(3-(allyloxy)-1-(3-methoxyphenyl)propylamino)-3-amino-4-phenylbutan-2-olYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. extractionthe product was extracted with EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-36f29ebd806949619056cfdeb9199309
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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