HCID 66857639, compound → HCID 66857976, compound

HRID 2037681Notes

Reaction equation

HRID 2037681 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:29][CH2:30][CH2:31][OH:32])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CC(C)=[O:35].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:29][CH2:30][C:31]([OH:35])=[O:32])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:27])([F:26])[F:28])=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66857639HCID 66857639, compoundHCID 131709961Jones' reagent

Product 1

HCID 66857976HCID 66857976, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (320 mg, 0.7 mmol) in acetone (7 mL) was added Jones reagent (2.5 M□1.05 mL) at 0° C. The mixture was stirred at this temperature for 30 min. The formed mixture was filtered and the filtrate was concentrated. The residue was treated with H2O (10 mL) and CH2Cl2 (10 mL). The mixture was separated, and the organic layer was washed with brine and concentrated. The residue was purified by preparative TLC to give 3-((R)-6-(4-fluorophenyl)-2-oxo-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-6-yl)propanoic acid (290 mg, 88%).

Workup

  1. filtrationThe formed mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was treated with H2O (10 mL) and CH2Cl2 (10 mL)
  4. customThe mixture was separated
  5. washthe organic layer was washed with brine
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-2d888906d4fd410cb24b86a9d72098c9
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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