Lawesson's reagent → HCID 86671883, compound

HRID 331148Notes

Reaction equation

HRID 331148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C@:16]3([CH3:28])[C:22]([F:24])([F:23])[C:21]([CH3:26])([CH3:25])[O:20][CH2:19][C:18](=O)[NH:17]3)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C@:16]3([CH3:28])[C:22]([F:24])([F:23])[C:21]([CH3:26])([CH3:25])[O:20][CH2:19][C:18](=[S:38])[NH:17]3)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380567HCID 68380567, compound

Product 1

HCID 86671883HCID 86671883, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-5-(3′,5′-dichloro-4-fluoro-biphenyl-3-yl)-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-one (250 mg, 578 μmol) with Lawesson's reagent (187 mg, 463 μmol) in 1,4-dioxane (19 ml) yielded the (R)-5-(3′,5′-dichloro-4-fluoro-biphenyl-3-yl)-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (202 mg, 78% yield) as a white foam. MS (ISN): m/z=446.0 [M−H]− and 447.9 [M+2-H]−.

Sources & evidence

ORD record
ord-1c518d79377345488f460dba04979fa2
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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