Lawesson's reagent → (R)-6,6-Difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-[1,4]oxazepane-3-thione

HRID 331167Notes

Reaction equation

HRID 331167 reaction equation
[F:1][C:2]1([F:21])[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]([I:19])[CH:16]=[CH:15][C:14]=1[F:20])[CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>>[F:1][C:2]1([F:21])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[S:31])[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:14]=1[F:20])[CH3:12]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 68380642(R)-6,6-difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-[1,4]oxazepan-3-one

Product 1

HCID 86671892(R)-6,6-Difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-[1,4]oxazepane-3-thioneYield 95.3%

Procedure

In a manner analogous to that described for the preparation of intermediate B7, the reaction of (R)-6,6-difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-[1,4]oxazepan-3-one (intermediate B6″.1) (1.455 g, 3.52 mmol) with Lawesson's reagent (1.42 g, 3.52 mmol), yielded the title compound (1.44 g, 95% yield) as a colorless oil. MS (ISP): m/z=430.1 [M+H]+.

Sources & evidence

ORD record
ord-74bbdd025eba46dd8f92fe991790ddc4
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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