HCID 68718908, compound → HCID 68712703, compound

HRID 506332Notes

Reaction equation

HRID 506332 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@H:9]([NH:18]C(O[C@H](C2C=CC=CC=2)C)=O)[CH2:8][C@@H:7]1[CH2:30][CH3:31])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@H:9]([NH2:18])[CH2:8][C@@H:7]1[CH2:30][CH3:31])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 68718908HCID 68718908, compound

Product 1

HCID 68712703HCID 68712703, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ten % palladium/carbon (100 mg) is added to a solution (10 ml) of (2S,4R)-2-ethyl-6-methoxy-4-[(S)-1-phenylethoxycarbonylamino]-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (1.00 g) in ethanol, and the mixture is stirred for 3 hours under hydrogen. Palladium/carbon is removed by filtration, and the filtrate is concentrated under reduced pressure to give (2S,4R)-4-amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (619 mg). MS (m/z): 280 [M+H]+

Workup

  1. customPalladium/carbon is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf3a262548ec4866b831b1bb97ea6360
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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