4-Chlorobenzenesulfonyl chloride → (2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methoxybenzyl)amino]-4-methylpentanoic acid amide

HRID 1893831노트

반응식

HRID 1893831 반응식
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[O:11])=[CH:5][CH:4]=1.CCN(CC)CC.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:8]([C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[O:11])[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 59432820(2R)-2-(4-Methoxybenzylamino)-4-methylpentanoic acid amide

생성물 1

HCID 9867067(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methoxybenzyl)amino]-4-methylpentanoic acid amide수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2R)-2-[N-(4-Methoxybenzyl)amino]-4-methylpentanoic acid amide (3.57 g, 14.3 mmol) was dissolved in CH2Cl2 (100 mL) and treated with Et3N (4.2 mL, 29 mmol) and 4-chlorobenzenesulfonyl chloride (3.6 g, 17 mmol) at rt for 18 h. The solvents were removed and the residue was taken into EtOAc (500 mL). The organic solution was washed with H2O, brine, dried over MgSO4, and concentrated. The resulting material was then further purified by flash chromatography (SiO2, 1% MeOH/CH2Cl2) to afford the title compound (2.4 g) as a slightly colored solid in 40% yield. MS (ESI), (M−H)−422.9; 1H NMR (CDCl3) δ 7.63 (d, 2H, J=7.0), 7.42 (d, 2H, J=7.0), 7.25 (d, 2H, J=8.0), 6.79 (d, 2H, J=8.0), 6.25 (br s, 1H), 5.35 (br s, 1H), 4.36 (dd, 2H, J=5.0, 15), 4.26 (t, 1H, J=7.2), 3.78 (s, 3H), 1.83 (m, 1H), 1.18-1.34 (m, 2H), 0.75 (d, 3H, J=7.0), 0.67 (d, 3H, J=7.0); IR (KBr) 3480, 2959, 1693, 1674, 1514, 1333, 1158 cm−1.

후처리

  1. customThe solvents were removed
  2. washThe organic solution was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting material was then further purified by flash chromatography (SiO2, 1% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-a174395c3b024321a0908baca94bb24d
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513253B2

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