Lithium Hydroxide → HCID 11805816, compound

HRID 225849Notes

Reaction equation

HRID 225849 reaction equation
C(OC([N:8]1[C:17]2[N:16]=[CH:15][C:14](/[CH:18]=[CH:19]/[C:20]([O:22]CC3C=CC=CC=3)=[O:21])=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.[Li+].[OH-]>Cl.O1CCOCC1>[N:16]1[C:17]2[NH:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[C:14](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])[CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10938089HCID 10938089, compound

Product 1

HCID 11805816HCID 11805816, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzyl (E)-3-[8-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro1,8-naphthyridin-3-yl]acrylate (1.21 g, 3.07 mmole) was dissolved in 4 N HCl in dioxane (15 mL). After 18 hr the mixture was concentrated. The residue was taken up in 1:1 MeOH/H2O (15 mL). 1.0 N LiOH (15 mL, 15 mmole) was added and the mixture heated to reflux. After 18 hr the mixture was cooled to RT and concentrated to approximately ⅓ volume. The mixture was adjusted to pH 6 using 10% HCl. The solid was collected by filtration, washed with H2O, and dried in vacuo to give the title compound (180 mg, 29% over 2 steps): MS (ES) m/e 205 (M+H)+.

Workup

  1. concentrationAfter 18 hr the mixture was concentrated
  2. temperaturethe mixture heated to reflux
  3. concentrationconcentrated to approximately ⅓ volume
  4. filtrationThe solid was collected by filtration
  5. washwashed with H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a8ca22c8a2db4f73928b2ca0b6cff067
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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