Lawesson's reagent → (R)-6,6-difluoro-5-(2-fluoro-5-(tetrahydro-2H-pyran-4-yl)phenyl)-5,7,7-trimethyl-1,4-oxazepan-3-thione

HRID 331145Notes

Reaction equation

HRID 331145 reaction equation
[F:1][C:2]1([F:26])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=O)[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[CH:15][C:14]=1[F:25])[CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCOCC1>[F:1][C:2]1([F:26])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[S:36])[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[CH:15][C:14]=1[F:25])[CH3:12]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380531(R)-6,6-difluoro-5-(2-fluoro-5-(tetrahydro-2H-pyran-4-yl)phenyl)-5,7,7-trimethyl-1,4-oxazepan-3-one

Product 1

HCID 86671881(R)-6,6-difluoro-5-(2-fluoro-5-(tetrahydro-2H-pyran-4-yl)phenyl)-5,7,7-trimethyl-1,4-oxazepan-3-thioneYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-6,6-difluoro-5-(2-fluoro-5-(tetrahydro-2H-pyran-4-yl)phenyl)-5,7,7-trimethyl-1,4-oxazepan-3-one (244 mg, 657 μmol) with Lawesson's reagent (266 mg, 657 μmol) in 1,4-dioxane (20 ml) yielded the (R)-6,6-difluoro-5-(2-fluoro-5-(tetrahydro-2H-pyran-4-yl)phenyl)-5,7,7-trimethyl-1,4-oxazepan-3-thione (205 mg, 81% yield) as a white foam. MS (ISP): m/z=388.2 [M+H]+.

Sources & evidence

ORD record
ord-fe1d8739c07545e69cb995868c9fac9a
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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