Hydrochloric Acid → HCID 15458709, compound

HRID 990343Notes

Reaction equation

HRID 990343 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.[O:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[H][H]>C(O)C.O.[Pd]>[CH3:5][CH:4]([CH3:6])[CH2:3][C@H:2]([NH:1][CH:14]1[CH2:15][CH2:16][O:11][CH2:12][CH2:13]1)[C:7]([OH:9])=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6106L-LeucineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15458709HCID 15458709, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of L-leucine (20.0 g, 152 mmol), concentrated aqueous HCl solution (13.1 mL, 36.5%), and tetrahydro-4H-pyran-4-one (30.0 g, 300 mmol, Aldrich, Milwaukee, Wis.) was agitated in an atmosphere of hydrogen (pressure, 43-51 psi) at room temperature in a mixture of ethanol and water (1:1, v/v, 400 mL) in the presence of Pd/C (20%, 4 g) until the absorption of hydrogen almost ceased, filtered. The filtrate was treated with concentrated aqueous ammonium hydroxide (29.8%) to adjust the pH to 5.5. White solid precipitated out which was isolated via filtration. The white solid was mixed with 150 mL of water and heated to boiling. After cooling down to 0° C., the white solid was filtered and dried under vacuum affording 17.5 g (53.4%) of the pure titled compound as a white solid; mp >300° C. APCI-MS m/z 216.2 (MH+).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was treated with concentrated aqueous ammonium hydroxide (29.8%)
  3. customWhite solid precipitated out which
  4. customwas isolated via filtration
  5. temperatureheated to boiling
  6. filtrationthe white solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-620721cea13a480da066d04a19771bc1
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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