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 1925498ノート

反応式

HRID 1925498 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d2cef9184e2f4240a542aa75b18cd8fa
出典データセット
uspto-grants-2012_05
特許番号
US08178679B2

反応ノート

読み込み中…