Hydrochloric Acid → HCID 69058423, compound

HRID 1817336Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16]([O:18]CC)=[O:17])=[N:11][CH:10]=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22].[Li+].[OH-].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16]([OH:18])=[O:17])=[N:11][CH:10]=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (27.0 g, 71 mmol) in THF (333 mL) and MeOH (166 mL) was added LiOH (5.21 g, 214 mmol) dissolved in enough water to make a 1N solution (total volume 213 mL) and the reaction was heated to 60° C. overnight. HPLC showed completion. A white precipitate was observed. The reaction was neutralized with 1N HCl and the more volatile solvents removed, leaving the water solution. 300 mL water was added the solution was acidified to pH 1 with 1 N HCl. A large amount of solids had precipitated. The resulting slurry was stirred vigorously with 100 mL CHCl3. Most of the solid had precipitated from the partitioning and the entire mix was filtered and dried over the weekend to give product. Additional less pure product was recovered from extraction of the filtrate.

Workup

customthe more volatile solvents removed
customleaving the water solution
customA large amount of solids had precipitated
customMost of the solid had precipitated from the partitioning and the
additionentire mix
filtrationwas filtered
customdried over the weekend
customto give product
customAdditional less pure product was recovered from extraction of the filtrate

Sources & evidence

ORD record: ord-db25fbb1b1d24769928dc3c548ebf0fc
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598264B2

Reaction notes

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