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Triethylamine → (3R,4S)-1-[4-(3-aminoprop-1-yn-1-yl)phenyl]-4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

HRID 1437823
ノート
印刷プレビュー

反応式

HRID 1437823 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[N:18]([C:19]3[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=3)[C:17](=[O:26])[C@@H:16]2[CH2:27][CH2:28][C@@H:29]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[OH:30])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:38]([NH2:41])[C:39]#[CH:40].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[NH2:41][CH2:38][C:39]#[C:40][C:22]1[CH:23]=[CH:24][C:19]([N:18]2[C@H:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:10][CH:11]=3)[C@@H:16]([CH2:27][CH2:28][C@@H:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[OH:30])[C:17]2=[O:26])=[CH:20][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 68977003(3R,4S)-4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-iodophenyl)azetidin-2-one

生成物 1

HCID 68976050(3R,4S)-1-[4-(3-aminoprop-1-yn-1-yl)phenyl]-4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 8 mg (0.013 mmol, 1 equiv.) (3R,4S)-4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-iodophenyl)azetidin-2-one (intermediate step A) in 0.5 mL DMF was added 2.2 mg (0.002 mmol, 0.15 equiv.) tetrakistriphenylphosphine palladium(0) and 0.8 mg (0.004 mmol, 0.3 equiv) copper(I) iodide. The solution was deoxygenated by a slow stream of anhydrous nitrogen delivered by a needle through a rubber septum. To the resulting solution was added by syringe 0.012 mL (0.177 mmol, 14 equiv.) propargyl amine and 0.012 mL (0.09 mmol, 7 equiv.) triethylamine. The resulting solution was stirred at room temperature for 1.25 hr at which time the solvent was removed under vacuum. The residue was purified by prep. Tlc eluting with CH2Cl2/MeOH (9/1) to afford the title compound. m/z (ES) 559.3 (MH+), 542.3 (MH−NH3+).

後処理

  1. customThe solution was deoxygenated by a slow stream of anhydrous nitrogen
  2. customwas removed under vacuum
  3. customThe residue was purified by prep

出典と根拠

ORDレコード
ord-6ffc8fc9f27e43df965de51daa7498aa
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07622449B2

反応ノート

読み込み中…

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