Lithium Hydroxide → (E)-3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid

HRID 1361939Notes

Reaction equation

HRID 1361939 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[C:15](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])[CH:16]=[N:17][C:9]1=2)=O)(C)(C)C.[Li+].[OH-]>Cl.O1CCOCC1>[O:11]1[CH2:12][CH2:13][NH:8][C:9]2[N:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:14][C:10]1=2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22139159(E)-3-[4(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-7-yl]acrylic acid

Product 1

HCID 22139122(E)-3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acidYield 52%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(E)-3-[4-(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-7-yl]acrylic acid (1.17 g, 2.95 mmole) was dissolved in 4 N HCl in dioxane (15 mL). After 72 hr the mixture was concentrated. The residue was taken up in 1:1 MeOH/H2O (20 mL). 1.0 N LiOH (15 mL, 15 mmole) was added and the mixture was 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 (315 mg, 52% over 2 steps): MS (ES) m/e 207 (M+H)+.

Workup

  1. concentrationAfter 72 hr the mixture was concentrated
  2. temperaturethe mixture was 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-6d3b6b300baf408e9e3d9e1e2493dd7a
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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