Triethylamine → HCID 66671463, compound

HRID 446576Notes

Reaction equation

HRID 446576 reaction equation
[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:43])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:42])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH3:34])=[CH:29][CH:28]=2)[CH3:19])[CH2:12][CH2:11]1.C(N(CC)CC)C.[C:57](Cl)(=[O:66])[O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:20](=[O:42])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:27]2[CH:28]=[CH:29][C:30]([N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[CH3:34])=[CH:31][CH:32]=2)[C:57](=[O:66])[O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH2:12][CH2:11]1)=[O:43]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformate2×HCID 516892Sodium Bicarbonate2×HCID 66671689HCID 66671689, compound

Product 1

HCID 66671463HCID 66671463, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

The compound (257 mg, 0.383 mmol) obtained in Example 83b was dissolved in dichloromethane (4 mL), triethylamine (107 mL, 0.766 mmol) and benzyl chlorocarbonate (0.082 mL, 0.58 mmol) were added, and the mixture was stirred at 50° C. for 2 hours. A saturated aqueous sodium hydrogencarbonate solution was added, the mixture was extracted with methylene chloride (×3), and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was dissolved in tetrahydrofuran (4 mL), 55% sodium hydride-paraffin (25.0 mg, 0.573 mmol) and benzyl chlorocarbonate (0.082 mL, 0.58 mmol) were added, and the mixture was stirred. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and dichloromethane was further added to separate the layers. The resulting organic layer was separated and dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography to give the title compound (235 mg; yield, 76%) as a brown oily substance.

Workup

  1. extractionthe mixture was extracted with methylene chloride (×3)
  2. dry with materialthe resulting organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in tetrahydrofuran (4 mL)
  5. stirringthe mixture was stirred
  6. additionwas further added
  7. customto separate the layers
  8. customThe resulting organic layer was separated
  9. dry with materialdried with anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-918c347569a24117b6e32c34e245a9d5
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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