Water → HCID 58109484, compound

HRID 2037515Notes

Reaction equation

HRID 2037515 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O.O.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C@@H:33]([N:35]3[CH2:40][CH2:39][C@:38]([CH2:47][CH2:48][CH2:49][OH:50])([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[O:37][C:36]3=[O:51])[CH3:34])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1>CC(C)=O>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][C:30]([C@@H:33]([N:35]3[CH2:40][CH2:39][C@:38]([CH2:47][CH2:48][C:49]([OH:3])=[O:50])([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[O:37][C:36]3=[O:51])[CH3:34])=[CH:31][CH:32]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 53473137HCID 53473137, compoundHCID 131709961Jones' reagent2×

Product 1

HCID 58109484HCID 58109484, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

CrO3 (1 g) was added to H2SO4 (1 mL) and water was added to bring the total volume to 4 mL. (R)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (600 mg, 1.4 mmol) was dissolved in 10 mL acetone, and cooled in an ice bath. The Jones reagent (0.5 mL) was slowly added to the mixture and stirred overnight. Solvent was removed in vacuo, the residue was dissolved in CH2Cl2 (10 mL) and water (10 mL). The layers were separated, and the aq layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give 3-((R)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanoic acid (500 mg, crude), which was not purified.

Workup

  1. additionwas added
  2. temperaturecooled in an ice bath
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  5. customThe layers were separated
  6. extractionthe aq layer was extracted with CH2Cl2 (3×10 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4b22d7882b4447a093a8a71a45c10e20
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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