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

HRID 1696850노트

반응식

HRID 1696850 반응식
[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

참가 물질

4

반응물 1

HCID 58100142HCID 58100142, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-01511e8a109847278242ff904fd3d2bc
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163758B2

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