L-Leucine → HCID 15481774, compound

HRID 433533Notes

Reaction equation

HRID 433533 reaction equation
N[C@H](C(O)=O)[CH2:3][CH:4]([CH3:6])[CH3:5].C(=O)(O)[O-].[Na+].C1(CC(Cl)=O)C=CC=CC=1.[C:25]1([CH2:31][C:32]([NH:34][C@H:35]([C:40]([OH:42])=[O:41])[CH2:36][CH:37]([CH3:39])[CH3:38])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCOCC1.C(OCC)(=O)C.C(Cl)(Cl)Cl.C(O)C(C)C>[CH2:3]([O:41][C:40](=[O:42])[C@H:35]([CH2:36][CH:37]([CH3:39])[CH3:38])[NH:34][C:32](=[O:33])[CH2:31][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:4]([CH3:6])[CH3:5]

Participants

9

Reactant 4

HCID 6106L-LeucineHCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 11983894N-Phenylacetyl-L-leucine

Product 1

HCID 15481774HCID 15481774, compound

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6560IsobutanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

L-Leucine (Aldrich) (0.114 g, 0.869 mmols) was taken-up in dioxane (5.0 mL) and treated with a saturated solution of sodium bicarbonate (5.0 mL) followed by phenylacetyl chloride (Aldrich) (0.114 mL, 0.822 mmols). After stirring for 17 hours at room temperature the mixture was diluted with ethyl acetate, the layers separated and the aqueous layer acidified to pH 2 with 5N HCl. The crude product was extracted into ethyl acetate, dried over sodium sulfate, vacuum dried and used without further purification. N-Phenylacetyl-L-leucine (0.0081 g, 0.038 mmol) was dissolved in 2.0 mL CHCl3 (EtOH free) and iso-butyl alcohol (0.055 mL) and treated with P-EPC (100 mg, 0.87 milliequivalents). The mixture was rotated for 4 days, filtered through a plug of cotton and the filtrate evaporated at reduced pressure to an oil which was sufficiently pure for testing.

Workup

  1. customthe layers separated
  2. extractionThe crude product was extracted into ethyl acetate
  3. dry with materialdried over sodium sulfate, vacuum
  4. customdried
  5. customused without further purification
  6. waitThe mixture was rotated for 4 days
  7. filtrationfiltered through a plug of cotton
  8. customthe filtrate evaporated at reduced pressure to an oil which

Sources & evidence

ORD record
ord-3e5b2aa52fb24f9c9b912842c0397795
Source dataset
uspto-grants-2003_12
Patent number
US06667305B1

Reaction notes

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