Hydrochloric Acid → benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidine-1-carboxylate

HRID 431760노트

반응식

HRID 431760 반응식
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][N:19]3[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:34]I.[H-].[Na+].Cl>CN(C=O)C>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([O:23][CH3:34])[CH2:20][N:19]3[C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86759290benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 86759293benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (400 mg) and CH3I (0.57 mL) in DMF (5 mL) was added NaH (60% oil suspension, 48 mg) at 5° C. The mixture was stirred at the same temperature for 10 minutes, then stirred at room temperature for 30 minutes. The reaction mixture was poured into diluted HCl, and extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate, water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 1:1 elution) to give benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidine-1-carboxylate (402.9 mg).

후처리

  1. stirringstirred at room temperature for 30 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water, saturated sodium hydrogen carbonate, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gal column chromatography (hexane-EtOAc, 1:1 elution)

출처 및 근거

ORD 기록
ord-1b61353a2a1d4208a93c460c40c7c014
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660759B1

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