Water → HCID 57672871, compound

HRID 73849Notes

Reaction equation

HRID 73849 reaction equation
C1(CO[C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:24][OH:25])[CH:21]([CH3:23])[CH3:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])C=CC=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+].[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1C(Cl)=O>CO.C(OCC)(=O)C.[C].[Pd]>[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:24][OH:25])[CH:21]([CH3:22])[CH3:23])=[O:18])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:10]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 682422-Furancarbonyl chlorideHCID 57672846N-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-L-valinol

Product 1

HCID 57672871HCID 57672871, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

30 mg of 10% palladium-carbon was added to a solution of 350 mg (1 mmol) of N—[N-[(phenylmethoxy)carbonyl]-L-leucyl]-L-valinol obtained in Reference Example 184 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. 10 ml of ethyl acetate, 10 ml of water and further 159 mg (1.5 mmol) of sodium carbonate were added to the residue. Under ice-cooling, a solution of 131 mg (1 mmol) of 2-furancarbonyl chloride in 3 ml of ethyl acetate was added to the mixture solution. The reaction solution was returned to room temperature and was stirred overnight. The aqueous layer of the reaction solution was separately collected and extracted with ethyl acetate. The organic layer was combined and after it was washed with a 10% potassium hydrogensulfate and then saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and ether was added to the residue to wash the crystal to obtain 268 mg (86%) of the title compound.

Workup

  1. filtrationAfter the reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. temperatureUnder ice-cooling
  4. customwas returned to room temperature
  5. stirringwas stirred overnight
  6. customThe aqueous layer of the reaction solution was separately collected
  7. extractionextracted with ethyl acetate
  8. washafter it was washed with a 10% potassium hydrogensulfate
  9. dry with materialsaturated brine, it was dried with anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure and ether
  11. additionwas added to the residue
  12. washto wash the crystal

Sources & evidence

ORD record
ord-4c76672ed7214cec939aabeedb7493a3
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

Loading…