HCID 58100142、化合物 → (4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl ester

HRID 1696850ノート

反応式

HRID 1696850 の反応式
[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][CH2:24][N:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[OH-].[OH-].[Pd+2]>[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:26](=[O:35])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]2=[O:34])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 58100142HCID 58100142、化合物

生成物 1

HCID 66860915(4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl ester収率 80%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension containing 58 (6.0 g, 12.59 mmol) and palladium dihydroxide (20% Pd(OH)2 on carbon, 50% wet, 3.0 g, 21.43 mmol) dissolved in anhydrous tetrahydrofuran 75 mL) was bubbled with nitrogen for 20 min. The reaction mixture was vacuumed, then charged with H2 gas (45 psi), and allowed to stir at rt for 24 h. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 59 (4.88 g, 80%) as a thick, brown oil: 1H NMR (500 MHz, CDCl3) δ 7.85 (dd, 2H), 7.74 (dd, 2H), 7.35-728 (m, 6H), 7.06 (d, 4H), 3.70 (t, 2H), 3.19 (t, 2H), 2.63-2.56 (m, 4H), 2.00 (d, 2H), 1.73-1.50 (m, 8H); m/z (ESI) 485 [C30H32N2O4+H]+.

後処理

  1. customwas bubbled with nitrogen for 20 min
  2. additioncharged with H2 gas (45 psi)
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with 0-100% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-01511e8a109847278242ff904fd3d2bc
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

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