Dichloromethane → HCID 11745779, compound

HRID 1052196Notes

Reaction equation

HRID 1052196 reaction equation
ClCCl.Cl.[NH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7]O.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(N(CC)CC)C>[C:14]1([C:13]([NH:5][C:6](=[CH2:7])[C:9]([O:11][CH3:12])=[O:10])=[O:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 11745779HCID 11745779, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To dichloromethane (400 mL) were added methyl serinate hydrochloride (45.0 g) and triethylamine (132 mL), and benzoyl chloride (77.0 mL) was added dropwise. After stirring at room temperature overnight, the reaction system was washed twice with saturated aqueous sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane (300 mL), and 2,3,4,6,7,8,9,10-octahydroprimido[1,2-a]azepine(52.0 g) was added. The mixture was stirred at room temperature for 4 hr, and the reaction system was washed twice with water and saturated aqueous sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give a crude product (67.0 g) of the title compound as a brown oil.

Workup

  1. additionwas added dropwise
  2. washthe reaction system was washed twice with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customInsoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (300 mL)
  7. addition2,3,4,6,7,8,9,10-octahydroprimido[1,2-a]azepine(52.0 g) was added
  8. stirringThe mixture was stirred at room temperature for 4 hr
  9. washthe reaction system was washed twice with water and saturated aqueous sodium hydrogen carbonate
  10. dry with materialdried over anhydrous sodium sulfate
  11. customInsoluble material was removed by filtration
  12. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ee34f9cf659489687756da8c49cfe52
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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