Lawesson's reagent → (R)-5-(5-(3,6-dihydro-2H-pyran-4-yl)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione

HRID 331141Notes

Reaction equation

HRID 331141 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([F:26])=[C:11]([C@:13]3([CH3:25])[C:19]([F:21])([F:20])[C:18]([CH3:23])([CH3:22])[O:17][CH2:16][C:15](=O)[NH:14]3)[CH:12]=2)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCOCC1>[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([F:26])=[C:11]([C@:13]3([CH3:25])[C:19]([F:21])([F:20])[C:18]([CH3:23])([CH3:22])[O:17][CH2:16][C:15](=[S:36])[NH:14]3)[CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380032(R)-5-(5-(3,6-dihydro-2H-pyran-4-yl)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one

Product 1

HCID 86671878(R)-5-(5-(3,6-dihydro-2H-pyran-4-yl)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thioneYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-5-(5-(3,6-dihydro-2H-pyran-4-yl)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one (72 mg, 195 μmol) with Lawesson's reagent (79 mg, 195 μmol) in 1,4-dioxane (5 ml) yielded the (R)-5-(5-(3,6-dihydro-2H-pyran-4-yl)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione (65 mg, 87% yield) as a white foam. MS (ISP): m/z=386.0 [M+H]+.

Sources & evidence

ORD record
ord-2ec9e33c1ecd4635bbb34d94172f6f9f
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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