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

HRID 501686

反応式

HRID 501686 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-36f29ebd806949619056cfdeb9199309
出典データセット
uspto-grants-2010_08
特許番号
US07772221B2

関連ノート

読み込み中…