Methane → HCID 69820406, compound

HRID 1840530Notes

Reaction equation

HRID 1840530 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C@H:12]([NH:23]C(OCC2C=CC=CC=2)=O)[C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[N:8][CH:9]=1)([O-])=O.C.[H][H]>CO.O.[Pd]>[NH2:23][C@@H:12]([CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][N:8]=1)[C:13]([OH:15])=[O:14]

Participants

7

Reactant 3

HCID 297MethaneHCID 86590140HCID 86590140, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69820406HCID 69820406, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5.16 g (11.5 mmol) of phenylmethyl (S)-5-nitro-α-[[(phenylmethoxy)carbonyl]amino]-2-pyridinebutanoate, 2 g of active charcoal and 0.77 g of active palladium-on-charcoal in 100 ml of methanol and 100 ml of water is stirred for 4 days at 50 psi of hydrogen at room temperature. The reaction medium is filtered through a cake of Celite and the cake is rinsed with 3×50 ml of boiling water. The aqueous phases are combined and concentrated under reduced pressure. 2.05 g of (S)-α,5-diamino-2-pyridinebutanoic acid are thus obtained in the form of a white solid.

Workup

  1. filtrationThe reaction medium is filtered through a cake of Celite
  2. washthe cake is rinsed with 3×50 ml of boiling water
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fad2d886ff9e41ce9023a9f25f503aed
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

Loading…