Di(succinimido) carbonate → HCID 178523862, 화합물

HRID 23367

반응식

HRID 23367 반응식
[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]

참가 물질

4

반응물 2

HCID 676246Di(succinimido) carbonateHCID 178511782HCID 178511782, 화합물

생성물 1

HCID 178523862HCID 178523862, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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 (br s, 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.

후처리

  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
  6. customto obtain a brown solid (215 mg 49%)

출처 및 근거

ORD 기록
ord-cb22f0548baf4d8d915a667decce0eb0
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852725B1

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