Oxygen → HCID 58109464, compound

HRID 2037592Notes

Reaction equation

HRID 2037592 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][CH:16]=[C:15]([Br:19])[CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].CN(C=[O:31])C.O=O>Cl[Pd]Cl.Cl[Cu].O>[Br:19][C:15]1[CH:14]=[C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@@:4]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)([CH2:1][C:2](=[O:31])[CH3:3])[O:9][C:8]2=[O:10])[CH3:12])[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 977OxygenHCID 6228DimethylformamideHCID 58109367HCID 58109367, compound

Product 1

HCID 58109464HCID 58109464, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

(R)-6-allyl-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (55 mg, 0.13 mmol), PdCl2 (6 mg, 0.3 equiv.), and CuCl (26 mg, 2.3 equiv.) were mixed with DMF (2 mL) and water (˜250 μL). A balloon of oxygen was attached to the flask and the mixture was stirred vigorously overnight. LC-MS found the reaction completed. The mixture was quenched by satd aq NH4Cl solution (2 mL), diluted with EtOAc (20 mL), washed by brine (7 mL), dried over Na2SO4. After filtration and concentration, the residue was purified by preparative HPLC to afford (S)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-oxopropyl)-1,3-oxazinan-2-one (49 mg, 86% yield). LC-MS (3 min) tR=1.76 min, m/z=434, 436 (M+1).

Workup

  1. customThe mixture was quenched by satd aq NH4Cl solution (2 mL)
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed by brine (7 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a9d7792f4af847c2a7cb5dba81efa337
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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