Water → HCID 66857740, compound

HRID 2037679Notes

Reaction equation

HRID 2037679 reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[C:27]([CH2:31]I)([F:30])([F:29])[F:28].[F-].[Cs+].O>CS(C)=O>[CH2:1]([C@@:4]1([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:31][C:27]([F:30])([F:29])[F:28])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 58109237HCID 58109237, compound

Product 1

HCID 66857740HCID 66857740, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-hydroxyphenyl)ethyl)-1,3-oxazinan-2-one (700 mg, 1.97 mmol), CF3CH2I (621 mg, 2.96 mmol) and CsF (360 mg, 2.37 mmol) in DMSO (10 mL) was heated under 120° C. overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative TLC to give (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (500 mg, 58%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-346375903a7b45d793644412a74b531c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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