Hydrochloric Acid → HCID 69066186, compound

HRID 1817314Notes

Reaction equation

HRID 1817314 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:24][CH3:25])[C:11](=[O:23])[N:12]([CH3:22])[C:13]=3[C:17]([O:19]CC)=[O:18])[C:8]2=[O:26])=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO.O.C1COCC1>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:24][CH3:25])[C:11](=[O:23])[N:12]([CH3:22])[C:13]=3[C:17]([OH:19])=[O:18])[C:8]2=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69058346HCID 69058346, compound

Product 1

HCID 69066186HCID 69066186, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (1.15 g, 2.96 mmol) in 1:1:1 MeOH/H2O/THF (15 mL) was added LiOH (0.37 g, 8.88 mmol) and the solution was stirred for 2 hours. A solution of 1 N HCl (8.9 mL) was added, the solution was concentrated and CHCl3 and 10% KHSO4 were added. The layers were separated and the aqueous was extracted repeatedly. The combined organic layers were filtered and the solid collected. The remaining organic was dried over Na2SO4, filtered, combined with the collected solid and evaporated to give the crude product.

Workup

  1. concentrationthe solution was concentrated
  2. additionCHCl3 and 10% KHSO4 were added
  3. customThe layers were separated
  4. extractionthe aqueous was extracted repeatedly
  5. filtrationThe combined organic layers were filtered
  6. customthe solid collected
  7. dry with materialThe remaining organic was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a8c82beedc9f433fa9020ad03b319530
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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