HCID 10882014, compound → HCID 59302375, compound

HRID 2237374Notes

Reaction equation

HRID 2237374 reaction equation
C(OC([NH:11][C@H:12]([C:21]([O:23][CH3:24])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=1)=O)C1C=CC=CC=1>[Pd].C(O)C>[CH3:20][C:16]1[N:15]=[C:14]([CH2:13][C@@H:12]([C:21]([O:23][CH3:24])=[O:22])[NH2:11])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 10882014HCID 10882014, compound

Product 1

HCID 59302375HCID 59302375, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl N-(benzyloxycarbonyl)-3-(6-methylpyridin-2-yl)-L-alaninate (7.25 g, 22.1 mmol) [S. W. Jones, C. F. Palmer, J. M. Paul, P. D. Tiffin, Tetrahedron Lett. 1999, 40, 1211-1214] and 10 percent palladium on carbon (0.690 g) in ethanol (80 ml) is hydrogenated at RT and under atmospheric pressure for 1 h. The reaction mixture is passed through a syringe filter (Millipore, 0.45 μg, hydrophobic PTFE) which is washed with ethanol (2×10 ml). The residue is concentrated on a rotary evaporator (removal of solvent residues by entrainment with toluene, twice) and dried under high vacuum. The product is obtained as an oil (3.89 g, yield 91% of theory).

Workup

  1. customThe reaction mixture is passed through a syringe
  2. filtrationfilter (Millipore, 0.45 μg, hydrophobic PTFE) which
  3. washis washed with ethanol (2×10 ml)
  4. concentrationThe residue is concentrated on a rotary evaporator (
  5. customremoval of solvent residues by entrainment with toluene
  6. customtwice) and dried under high vacuum
  7. customThe product is obtained as an oil (3.89 g, yield 91% of theory)

Sources & evidence

ORD record
ord-689033be58e640b7b314ebb98064a7f1
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

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