Lawesson's reagent → HCID 86671876, compound

HRID 331137Notes

Reaction equation

HRID 331137 reaction equation
[F:1][C:2]1([F:28])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=O)[NH:4][C@:3]1([CH3:27])[C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH:15]=[CH:16][C:17]=1[F:18].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>O1CCOCC1>[F:1][C:2]1([F:28])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[S:38])[NH:4][C@:3]1([CH3:27])[C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380416HCID 68380416, compound

Product 1

HCID 86671876HCID 86671876, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-6,6-difluoro-5,7,7-trimethyl-5-(4,3′,5′-trifluoro-biphenyl-3-yl)-[1,4]oxazepan-3-one (159 mg, 398 μmol) with Lawesson's reagent (131 mg, 319 μmol) in 1,4-dioxane (13 ml) yielded the (R)-6,6-difluoro-5,7,7-trimethyl-5-(4,3′,5′-trifluoro-biphenyl-3-yl)-[1,4]oxazepan-3-thione (142 mg, 86% yield) as a white foam. MS (ISP): m/z=416.2 [M+H]+.

Sources & evidence

ORD record
ord-27e4406c4455456d9ffd5ede9d69ce6e
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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