(R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one → 3-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanoic acid

HRID 403583Notes

Reaction equation

HRID 403583 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C@@H:3]([N:5]1[CH2:10][CH2:9][C@@:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([CH2:11][CH2:12][CH2:13][OH:14])[O:7][C:6]1=[O:22])[CH3:4].CC(C)=[O:27].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:24][C:2]([CH3:23])([CH3:1])[C@@H:3]([N:5]1[CH2:10][CH2:9][C@:8]([CH2:11][CH2:12][C:13]([OH:27])=[O:14])([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[O:7][C:6]1=[O:22])[CH3:4]

Participants

4

Reactant 2

HCID 42623414(R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-oneHCID 131709961Jones' reagent

Product 1

HCID 584852693-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanoic acidYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (150 mg, 0.45 mmol) in acetone (10 mL) was added Jones reagent (2.5 mol/L, 0.5 mL) at 0° C., and the mixture was stirred at rt for 1 h. The reaction mixture was concentrated, and the mixture was extracted with EtOAc. The combined organic phase was concentrated to give the crude product, which was purified by preparative TLC to give 3-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanoic acid (50 mg, 32%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe mixture was extracted with EtOAc
  3. concentrationThe combined organic phase was concentrated
  4. customto give the crude product, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-9d9d8391a06d455ab0800d53d261a3cf
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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