HCID 14348567, compound → HCID 14167823, compound

HRID 655005Notes

Reaction equation

HRID 655005 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]([OH:10])=[O:9])[CH:6]([NH:11]CC2C=CC=CC=2)[CH:5]([CH3:19])[C:4](=[O:20])[O:3]1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][CH:2]1[CH:7]([C:8]([OH:10])=[O:9])[CH:6]([NH2:11])[CH:5]([CH3:19])[C:4](=[O:20])[O:3]1

Participants

5

Reactant 2

HCID 14348567HCID 14348567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14167823HCID 14167823, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(2SR,3SR,4RS,5RS)-Tetrahydro-2,5-dimethyl-6-oxo-4-benzylamino-2H-pyrane-3-carboxylic acid (100 mg) was dissolved in acetic acid (20 ml), and palladium hydroxidecarbon (prepared by the method as described in J.Am.Chem. Soc., 83, p.4798 (1961)) (20 mg) was added thereto. The resultant mixture was stirred at room temperature under hydrogen pressure of 3-4 kg/cm2 until the designed amount of hydrogen was consumed. The catalyst was collected by filtration and washed with water. The washing and the filtrate were combined together and concentrated at 40° C. under reduced pressure to give (2SR,3SR,4RS,5RS)-tetrahydro2,5-dimethyl-6-oxo-4-amino-2H-pyrane-3-carboxylic acid.

Workup

  1. addition, 83, p.4798 (1961)) (20 mg) was added
  2. customwas consumed
  3. filtrationThe catalyst was collected by filtration
  4. washwashed with water
  5. concentrationconcentrated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-197022e69c974d3684b634f909784bf0
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

Loading…