3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-isopropyl-1,3-oxazinan-2-one → 3-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoic acid

HRID 1096453Notes

Reaction equation

HRID 1096453 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]([CH2:19][CH2:20][CH2:21][OH:22])([CH:16]([CH3:18])[CH3:17])[O:12][C:11]2=[O:23])[CH3:9])=[CH:4][CH:3]=1.CC(C)=[O:26].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]([CH2:19][CH2:20][C:21]([OH:26])=[O:22])([CH:16]([CH3:17])[CH3:18])[O:12][C:11]2=[O:23])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 596357063-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-isopropyl-1,3-oxazinan-2-oneHCID 131709961Jones' reagent

Product 1

HCID 596357833-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-isopropyl-1,3-oxazinan-2-one. (41 mg, 0.1 mmol) in acetone (10 mL) was added Jones reagent (2.5 M, 1 mL) at 0° C. The mixture was stirred at room temperature for 1 h, concentrated, and extracted with EtOAc. The organic layer was concentrated to give the crude product 3-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoic acid (51 mg, 95% yield), which was used for the next step without further purification.

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-87f5db5c7dc64ed3b8cc9880da55181d
Source dataset
uspto-grants-2012_03
Patent number
US08138178B2

Reaction notes

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