Lawesson's reagent → HCID 86648760, compound

HRID 1425279Notes

Reaction equation

[C:1]([CH:4]([CH2:9][C:10]([N:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C@H:14]([O:29][CH3:30])[CH2:13]1)=O)[C:5]([O:7][CH3:8])=[O:6])(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH2:22]([O:21][C:19]([NH:18][C@H:15]1[CH2:16][CH2:17][N:12]([C:10]2[S:40][C:1]([CH3:2])=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=2)[CH2:13][C@H:14]1[O:29][CH3:30])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl cis(±)-2-acetyl-4-(4-{[benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-oxobutanoate obtained in Example (188b) (1.1 g) was dissolved in toluene. Lawesson's reagent (660 mg) was added, and the mixture was stirred at 110° C. for two hours. Further, Lawesson's reagent (330 mg) was added, and the mixture was stirred at 110° C. for two hours. The reaction solution was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10) and recrystallized from methylene chloride/hexane, to obtain 50 mg of the title compound as crystals.

Workup

stirringthe mixture was stirred at 110° C. for two hours
concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10)
customrecrystallized from methylene chloride/hexane

Sources & evidence

ORD record: ord-1fb906aa551e48148b289e631188efac
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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