Triethylamine → HCID 22928912, compound

HRID 2111663Notes

Reaction equation

HRID 2111663 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10].CN(C1C=CC=CN=1)C.[CH2:23]([NH:27][C:28]1[N:36]=[C:35]2[C:31]([N:32]=[C:33]([OH:46])[N:34]2[CH2:37][C:38]2[CH:39]=[N:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)=[C:30]([NH2:47])[N:29]=1)[CH2:24][CH2:25][CH3:26]>C(Cl)Cl.O>[CH2:23]([NH:27][C:28]1[N:36]=[C:35]2[C:31]([N:32]=[C:33]([O:46][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:34]2[CH2:37][C:38]2[CH:39]=[N:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)=[C:30]([NH2:47])[N:29]=1)[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 218852-DimethylaminopyridineHCID 178448882HCID 178448882, compound

Product 1

HCID 22928912HCID 22928912, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (100 μL, 0.75 mmol), ethyl chloroformate (67 μL, 0.70 mmol), and dimethylaminopyridine (20 mg, 0.17 mmol) were added to a solution (15 ml) of the compound (200 mg, 0.58 mmol) obtained in Example 19 in methylene chloride in that order, and the resultant was allowed to react at room temperature for 15 hours. Water was added to the reaction solution to extract an organic layer. The organic layer was washed with an aqueous solution of 5% citric acid and 10% saline solution and dried over anhydrous sodium sulfate. The solvent was then removed by distillation. Hexane was added to the residue, and the solid was precipitated, followed by collection by filtration. Thus, 170 mg of the title compound was obtained as a white powdery solid (yield: 71%).

Workup

  1. customto react at room temperature for 15 hours
  2. extractionto extract an organic layer
  3. washThe organic layer was washed with an aqueous solution of 5% citric acid and 10% saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation
  6. additionHexane was added to the residue
  7. customthe solid was precipitated
  8. filtrationfollowed by collection by filtration

Sources & evidence

ORD record
ord-b18f9a195c2d4a6193f296f3bc513650
Source dataset
uspto-grants-2009_04
Patent number
US07521454B2

Reaction notes

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