Triethylamine → N-[N-(4-Morpholinylcarbonyl)-L-leucyl]-L-norleucinol

HRID 1627469Notes

Reaction equation

HRID 1627469 reaction equation
C1(CO[C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:25][OH:26])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])C=CC=CC=1.C(N(CC)CC)C.[N:34]1(C(Cl)=O)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CO.C(Cl)Cl.[C].[Pd]>[N:34]1([C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:25][OH:26])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:18])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:10])[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 15168139N-[N-[(Phenylmethoxy)carbonyl]-L-leucyl]-L-norleucinol

Product 1

HCID 57672829N-[N-(4-Morpholinylcarbonyl)-L-leucyl]-L-norleucinolYield 71%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

70 mg of 10% palladium-carbon was added to a solution of 700 mg (2 mmol) of N—[N-[(phenylmethoxy)carbonyl]-L-leucyl]-L-norleucinol obtained in Reference Example 139 in 10 ml of methanol, and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. After the reaction solution was filtered, the filtrate was concentrated under reduced pressure. 20 ml of methylene chloride and 404 mg (4 mmol) of triethylamine were added to the residue. A solution of 299 mg (2 mmol) of 4-morpholinecarbonyl chloride in 3 ml of methylene chloride was added to the mixture solution under ice-cooling. The reaction solution was returned to room temperature and stirred overnight. After the reaction solution was washed with water and then saturated brine, it was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. Ether was added to the residue to wash it to obtain 488 mg (71%) of the title compound.

Workup

  1. filtrationAfter the reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. temperaturecooling
  4. customwas returned to room temperature
  5. stirringstirred overnight
  6. washAfter the reaction solution was washed with water
  7. dry with materialsaturated brine, it was dried with anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionEther was added to the residue
  10. washto wash it

Sources & evidence

ORD record
ord-791e28ca135d44df8b1cf4103057cdd9
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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