Sodium Iodide → [5-((1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(benzyloxy)phenyl]-formamide

HRID 1925498노트

반응식

HRID 1925498 반응식
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:38]Br)=[CH:33][C:32]=1[NH:48][CH:49]=[O:50])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[I-].[Na+].C(=O)([O-])O.[Na+]>CS(C)=O.O>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][CH2:38][C@@H:37]([C:34]4[CH:35]=[CH:36][C:31]([O:30][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[C:32]([NH:48][CH:49]=[O:50])[CH:33]=4)[O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:42])[CH3:43])=[CH:16][CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 574610672-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethaneHCID 67520640(2-{4-[2-(1-Adamantyl)ethoxy]phenyl}ethyl)amine

생성물 1

HCID 86649158[5-((1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(benzyloxy)phenyl]-formamide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

To a solution of Intermediate 22 (0.4 g, 1.34 mmol) and (R)—N-(2-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)phenyl)formamide (0.62 g, 0.82 mmol) in dimethyl sulfoxide (3 mL) was added sodium iodide (0.59 g, 3.99 mmol) and sodium hydrogen carbonate (0.67 g, 8.03 mmol). The reaction mixture was heated under argon at 130° C. for 1 hour. The mixture was poured into water and extracted with ether. The organic layer was washed with water and brine and the solvent was removed under reduced pressure. The title compound was obtained as yellow foam (0.84 g, 73%) and used in the next step without further purification. MS (M+): 684.

후처리

  1. extractionextracted with ether
  2. washThe organic layer was washed with water and brine
  3. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-d2cef9184e2f4240a542aa75b18cd8fa
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178679B2

반응 노트

불러오는 중…