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

HRID 501686

반응식

HRID 501686 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-36f29ebd806949619056cfdeb9199309
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

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