Di(succinimido) carbonate → HCID 178523862、化合物

HRID 230378

反応式

HRID 230378 の反応式
[NH2:1][C@@H:2]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:24]1[C:29](=[O:30])[N:28]([O:31][C:32](ON2C(=O)CCC2=O)=[O:33])[C:26](=[O:27])[CH2:25]1>C(#N)C>[O:27]=[C:26]1[CH2:25][CH2:24][C:29](=[O:30])[N:28]1[O:31][C:32]([NH:1][C@@H:2]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:33]

参加物

4

反応物 2

HCID 676246Di(succinimido) carbonateHCID 178511782HCID 178511782、化合物

生成物 1

HCID 178523862HCID 178523862、化合物収率 49%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

302.4 mg (1 mmol) of 2-{(1R)-1-amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole previously dissolved in 20 mL of anhydrous acetonitrile was added dropwise to a solution of N,N′-disuccinimidylcarbonate (528 mg, 2 mmol, DSC) in 20 mL of anhydrous acetonitrile during 1.5 hour. After a further 4 hours of stirring at room temperature, the solvent was evaporated in vacuo and the residue redissolved in 30 mL of chloroform. Excess DSC was then discarded and the organic layer washed with water (4×30 mL), dried over MgSO4 and concentrated to obtain a brown solid (215 mg, 49%). 1H-NMR (CDCl3, 100 MHz) δ: 8.22 (brs, 1H); 8.1-7.08 (m, 12H); 5.9 (br s, 1H); 4.97 (dd, J=3.6 and 9.3 Hz, 1H); 3.75 (dd, J=3.6 and 14.8 Hz, 1H), 3.06 (dd, J=9.7 and 14.6 Hz, 1H); 2.96 (s, 2H); 2.89 (s, 2H). LC/MS: m/z=329 ((M+H)−SuOH.

後処理

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue redissolved in 30 mL of chloroform
  3. washthe organic layer washed with water (4×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-055cded82b564de7b376687e76545765
出典データセット
uspto-grants-2009_07
特許番号
US07566734B2

関連ノート

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