Lithium Hydroxide → HCID 59843493, compound

HRID 1817366Notes

Reaction equation

HRID 1817366 reaction equation
C([O:4][C:5]1[N:6]=[C:7]([C:29]([O:31]CC)=[O:30])[C:8]2[CH2:9][CH2:10][N:11]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=3)[C:12](=[O:19])[C:13]=2[C:14]=1[O:15]C(=O)C)(=O)C.[OH-].[Li+]>C1COCC1.CO.O>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[F:27])[CH2:20][N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[C:14]([OH:15])[C:5](=[O:4])[NH:6][C:7]=2[C:29]([OH:31])=[O:30])[C:12]1=[O:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66997561HCID 66997561, compound

Product 1

HCID 59843493HCID 59843493, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ethyl 3,4-bis(acetyloxy)-6-(3-chloro-4-fluorobenzyl)-5-oxo-5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (1.00 g, 2.09 mmol; Example 12, step 8) and lithium hydroxide (0.70 g, 16.70 mmol) in a mixture of THF-methanol-water (30 mL, 1:1:1 by volume) was heated under reflux in an oil bath at 90° C. overnight. The product mixture was acidified and concentrated under vacuum. The residue was triturated with diethyl ether. The solid precipitated was filtered and washed with ether to provide the titled compound. ES MS M+1=367.

Workup

  1. temperaturewas heated
  2. concentrationconcentrated under vacuum
  3. customThe residue was triturated with diethyl ether
  4. customThe solid precipitated
  5. filtrationwas filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-e80110b68a4043ff98d58c248f3ddbb6
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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