Water → HCID 25182555, compound

HRID 2037413Notes

Reaction equation

HRID 2037413 reaction equation
[OH:1][S:2]([OH:5])(=[O:4])=[O:3].O.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:26][CH2:25][C:24]([CH2:33][CH2:34][OH:35])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:23][C:22]2=[O:36])[CH:16]=1.CC(C)=[O:39].OS(O)(=O)=O.[O:46]=[Cr:47](=[O:49])=[O:48]>CC(C)=O>[CH3:25][C:24]([CH3:27])=[O:23].[OH:4][S:2]([OH:5])(=[O:3])=[O:1].[O:46]=[Cr:47](=[O:49])=[O:48].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:26][CH2:25][C:24]([CH2:33][C:34]([OH:39])=[O:35])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:23][C:22]2=[O:36])[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 25182275HCID 25182275, compoundHCID 131709961Jones' reagent

Product 2

HCID 25182555HCID 25182555, compoundYield 19%HCID 131709961Jones' reagent

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent was prepared by addition of CrO3 (1 g) to H2SO4 (1 mL) and addition of water to bring the total volume to 4 mL. 3-(2′,4′-difluorobiphenyl-3-yl)-6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-2-one (100 mg, 0.24 mmol) was dissolved in acetone (2 mL), and cooled in an ice bath. Jones reagent (0.2 mL) was slowly added to the mixture and the reaction mixture was stirred overnight. Solvent was removed in vacuo and the obtained residue was purified by preparative HPLC to afford 2-(3-(2′,4′-difluorobiphenyl-3-yl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)acetic acid (20 mg, yield 19%). 1H NMR (400 MHz, CDCl3): δ=2.7-2.9 (m, 4H), 3.55 (m, 2H), 6.86 (m, 2H), 7.05 (m, 1H), 7.19 (m, 1H), 7.33 (m, 5H), 7.44 (m, 3H).

Workup

  1. temperaturecooled in an ice bath
  2. customSolvent was removed in vacuo
  3. customthe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-30b4f8bebd1f455aa18a5dd8baf24b8c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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