Sodium Hydroxide → HCID 22346270, compound

HRID 897285Notes

Reaction equation

HRID 897285 reaction equation
C[O:2][C:3]([C:5]1[C:14]([O:15]C(C2C=CC=CC=2)=O)=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7]([C:24]#[C:25][CH2:26][OH:27])[N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1.O>[OH:15][C:14]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([C:24]#[C:25][CH2:26][OH:27])=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20750084HCID 20750084, compound

Product 1

HCID 22346270HCID 22346270, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(3-hydroxy-prop-1-ynyl)-8-(1-phenyl-methanoyloxy)-[1,6]naphthyridine-7-carboxylic acid methyl ester (1.00 g, 2.76 mmol) in THF (14 mL) and water (14 mL) was added 1N NaOH (13.8 mL, 13.8 mmol) and the solution was stirred at 50° C. overnight. The THF was removed under reduced pressure and the remaining solution was acidified with 6N HCl to a pH=3. Injected the solution directly onto the Gilson auto-prep running a 95-50% H2O (0.1% TFA)/CH3CN (0.09% TFA) gradient over 35 minutes to obtain the desired compound as a bright yellow solid.

Workup

  1. customThe THF was removed under reduced pressure
  2. customover 35 minutes

Sources & evidence

ORD record
ord-21ab7614cf6e493fa0f261d110b76fb3
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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