Water → HCID 57672871, compound

HRID 1627470Notes

Reaction equation

HRID 1627470 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 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. 10 ml of ethyl acetate, 10 ml of water and further 159 mg (1.5 mmol) of sodium carbonate were added to the residue. A solution of 131 mg (1 mmol) of 2-furancarbonyl chloride in 3 ml of ethyl acetate was added to the mixture solution under ice-cooling. The reaction solution was returned to room temperature and was stirred overnight. The aqueous layer of reaction solution was separately collected and extracted with ethyl acetate. The organic layer was combined and after it was washed with 10% potassium hydrogensulfate and then saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, ether was added to the residue and the crystal was washed 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. temperaturecooling
  4. customwas returned to room temperature
  5. stirringwas stirred overnight
  6. customThe aqueous layer of reaction solution
  7. customwas separately collected
  8. extractionextracted with ethyl acetate
  9. washafter it was washed with 10% potassium hydrogensulfate
  10. dry with materialsaturated brine, it was dried with anhydrous sodium sulfate
  11. distillationThe solvent was distilled off under reduced pressure, ether
  12. additionwas added to the residue
  13. washthe crystal was washed

Sources & evidence

ORD record
ord-8a85648a848448009f0e181dd86586ed
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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