Lawesson's reagent → 6-Chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-2,3-dihydro-1'-[(tert-butoxycarbonyl)methyl]-2-oxo-6'-thioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1174056Notes

Reaction equation

HRID 1174056 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=O)[N:12]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:11]3[C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1.[CH3:41][O:42][CH:43]([Si:45]([CH3:48])([CH3:47])[CH3:46])[CH3:44].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:58]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[S:58])[N:12]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:11]3[C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1.[CH3:41][O:42][CH:43]([Si:45]([CH3:48])([CH3:47])[CH3:46])[CH3:44]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 775808616-Chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-2,3-dihydro-1'-[(tert-butoxycarbonyl)methyl]-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Product 1

HCID 867612126-Chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-2,3-dihydro-1'-[(tert-butoxycarbonyl)methyl]-2-oxo-6'-thioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of racemic (2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-2,3-dihydro-1′-[(tert-butoxycarbonyl)methyl]-2,6′-dioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (1 g, 1.4 mmol) prepared in example 1e and 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (1.5 g, 3.75 mmol) (Aldrich) in toluene (20 mL) was heated at 120° C. for 0.5 h. The mixture was cooled to room temperature and then concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:1) to give racemic (2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-2,3-dihydro-1′-[(tert-butoxycarbonyl)methyl]-2-oxo-6′-thioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a off white foam (Yield 1.0 g, 92%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (EtOAc:hexanes=1:1)

Sources & evidence

ORD record
ord-8e0c87b6fa394e7b87196867b5235f68
Source dataset
uspto-grants-2010_11
Patent number
US07834179B2

Reaction notes

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