HCID 68716650, compound → HCID 68718350, compound

HRID 506373Notes

Reaction equation

HRID 506373 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(OCC2C=CC=CC=2)=O)[CH2:8][C@H:7]1[CH3:29])=[O:5])[CH3:2]>C(O)C.O1CCCC1.[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[CH3:29])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 68716650HCID 68716650, compound

Product 1

HCID 68718350HCID 68718350, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2R*,4S*)-4-Benzyloxycarbonylamino-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (5.83 g) is dissolved in a mixture solvent of ethanol (60 ml) and tetrahydrofuran (60 ml), then thereto is added 10% palladium/carbon (500 mg), and the mixture is stirred at room temperature under hydrogen for 7 hours. The catalyst is removed by filtration, the filtrate is concentrated under reduced pressure to give (2R*,4S*)-4-amino-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (3.85 g). MS (m/z): 266 [M+H]+

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ceae790fe6d546ed8ebfe69c8242de9e
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

Loading…