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Dimethyl Sulfate → (2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methylaminobenzyl)amino]-4-methylpentanoic acid amide

HRID 1893834
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HRID 1893834 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:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28]CN(CC)CC.COS(OC)(=O)=O>C1(C)C=CC=CC=1>[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:18]=[CH:17][C:16]([NH:19][CH3:28])=[CH:15][CH:14]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 59001017(2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amide

생성물 1

HCID 59000964(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methylaminobenzyl)amino]-4-methylpentanoic acid amide수율 46%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of (2R)-2-[N-(4-chlorobenzenesulfonyl)-N-(4-aminobenzyl)amino]-4-methyl-pentanoic acid amide (Example 48, 400 mg, 1 mmol), Et3N (0.16 mL, 1.1 mmol), dimethylsulfate (139 mg, 1.1 mmol) in 25 mL of toluene was stirred at rt for 18 h. The reaction was concentrated, then taken into EtOAc and washed with H2O, brine, dried over K2CO3 and concentrated to give a crude mixture of starting material and product. The material was further purified by flash chromatography (SiO2, 35% EtOAc/hexanes) to afford the title compound, 195 mg, in 46% yield. MS (ESI), (M+H)+424.1; 1H NMR (CDCl3) δ 7.65 (d, 2H, J=8.0), 7.58 (d, 2H, J=8.2), 7.47 (d, 2H, J=8.0), 7.31 (d, 2H, J=8.5), 6.24 (br s, 1H), 5.16 (br s, 1H), 4.50 (dd, 2H, J=50, 17), 4.27 (t, 1H, J=10), 2.44 (s, 3H), 1.74-1.83 (m, 1H), 1.25-1.33 (m, 1H), 0.93-1.01 (m, 1H), 0.74 (d, 3H, J=7.0), 0.63 (d, 3H, J=7.0).

후처리

  1. concentrationThe reaction was concentrated
  2. washwashed with H2O, brine
  3. dry with materialdried over K2CO3
  4. concentrationconcentrated
  5. customto give a crude
  6. additionmixture of starting material and product
  7. customThe material was further purified by flash chromatography (SiO2, 35% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c7cfed94cd65462b8c76b78f902e7172
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08513253B2

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