Dimethylformamide → (2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-dimethylaminobenzyl)amino]-4-methylpentanoic acid amide

HRID 507302노트

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HRID 507302 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([NH2:23])=[O:22])[CH2:12][C:13]2[CH:18]=[CH:17]C(N)=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.IC.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O.[CH3:42][N:43]([CH:45]=O)[CH3:44]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([NH2:23])=[O:22])[CH2:12][C:13]2[CH:14]=[CH:15][C:45]([N:43]([CH3:42])[CH3:44])=[CH:17][CH:18]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 59001017(2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amide

생성물 1

HCID 59432818(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-dimethylaminobenzyl)amino]-4-methylpentanoic acid amide수율 16%

시약·촉매·용매 1

HCID 962Water용매

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온도
40 °C

실험 절차

(2R)-2-[N-(4-Chlorobenzene-sulfonyl)-N-(4-aminobenzyl)amino]-4-methyl-pentanoic acid amide (Example 48, 0.10 g, 0.22 mmol) was dissolved in DMF (5 mL). To this solution was added iodomethane (62 mg, 0.44 mmol), and cesium carbonate (220 mg, 0.66 mmol). The reaction was then stirred at 40° C. for 18 h. The reaction was poured into EtOAc and water. The organic was collected, dried over MgSO4, and concentrated to an oily residue. The residue was further purified (Biotage 40S, loaded in CH2Cl2, eluted in 25% EtOAc/hexanes) to yield a yellow powder (15 mg, 16%). MS (ESI), (M+H)+ 438.1; 1H NMR (DMSO-d6, 500 MHz) δ 7.74 (dd, 2H, J=1.9, 6.7), 7.54 (dd, 2H, J=1.9, 6.8), 7.43 (s, 1H), 7.16 (d, 2H, J=8.6), 7.01 (s, 1H), 6.61 (d, 2H, J=8.8), 4.59 (q, 2H, J=16, 25), 4.34 (dd, 1H, J=5.0, 9.3), 2.85 (s, 6H), 1.27-1.47 (m, 3H), 0.80 (d, 3H, J=5.9), 0.52 (d, 3H, J=6.1).

후처리

  1. customThe organic was collected
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to an oily residue
  4. customThe residue was further purified
  5. wash(Biotage 40S, loaded in CH2Cl2, eluted in 25% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-e0d66702db6d477f8c52402318ee4110
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786122B2

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