Sodium Hydroxide → HCID 58764043, compound

HRID 1438283Notes

Reaction equation

HRID 1438283 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[C:18]([F:26])[CH:17]=3)[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>Cl>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[C:18]([F:26])[CH:17]=3)[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58764009HCID 58764009, compound

Product 1

HCID 58764043HCID 58764043, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 4-[2-(2-cyclopentyl-4,6-dioxotetrahydro-2H-pyran-2-yl)ethyl]-2-fluorobenzoate (example B(5)) (300 mg) was treated with 4N NaOH (10 ml) and stirred for 4 hrs at room temperature. The mixture was then acidified with 1N HCl (20 ml) and the product was extracted with ethyl acetate (2×20 ml). The combined organic layers were dried over magnesium sulfate and concentrated to a solid. The solid was recrystallised from diethyl ether to afford the title compound as a white solid (120 mg). 1H NMR (300 MHz, MeOD): δ 1.38-2.30 (m, 11H), 2.80-3.12 (m, 6H), 6.91 (d, J=7.19 Hz, 1H), 7.17 (m, 1H), 7.86 (d, J=719 Hz, 1H)

Workup

  1. extractionthe product was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated to a solid
  4. customThe solid was recrystallised from diethyl ether

Sources & evidence

ORD record
ord-9a4ca7644df945ca9a6d595a87b683bd
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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