Di(succinimido) carbonate → HCID 178523862, compound

HRID 1869522Notes

Reaction equation

HRID 1869522 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 178523862HCID 178523862, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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 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.

Workup

  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%)

Sources & evidence

ORD record
ord-dbbbdbf6773b46b8886fbb4ab410c965
Source dataset
uspto-grants-2009_12
Patent number
US07638546B1

Reaction notes

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