Dimethylformamide → HCID 58109136, compound

HRID 2037578Notes

Reaction equation

HRID 2037578 reaction equation
[CH2:1]([C@@:4]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([F:22])[F:21])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].CN(C=[O:33])C>Cl[Cu].Cl[Pd]Cl>[F:21][CH:20]([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:1][C:2](=[O:33])[CH3:3])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58109210HCID 58109210, compound

Product 1

HCID 58109136HCID 58109136, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
30 °C

Procedure

To a solution of (R)-6-allyl-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (379 mg, 1 mmol) in DMF were added CuCl (227 mg, 2.3 mmol) and PdCl2 (53 mg, 0.3 mmol) at 0° C. under O2, and the mixture was stirred overnight at 30° C. The mixture was washed with water and extracted with EtOAc. The organic layer was separated, and concentrated to give the crude product, which was purified by preparative TLC to afford (S)-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(2-oxopropyl)-6-phenyl-1,3-oxazinan-2-one (180 mg, 50%).

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-32f49405531b4e60838bf1f869dfbd6f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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