Lawesson's reagent → HCID 12042586, compound

HRID 1018135Notes

Reaction equation

HRID 1018135 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:43]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 12042585HCID 12042585, compound

Product 1

HCID 12042586HCID 12042586, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 21840791Dioxane tolueneSolvent

Procedure

To a solution of N-[[1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester (1.00 g, 2.16 mmol) in toluene/dioxane (1: 1, 10 mL) was added Lawesson's reagent (0.524 g, 1.29 mmol). The resultant mixture was warmed to 50° C. and was stirred for 24 h. The reaction mixture was filtered through a sintered glass funnel and the filtrate was concentrated in vacuo. Purification of the crude product by silica gel flash column chromatography (hexane-ethyl acetate, 6:1 then 4:1), afforded N-[[1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]cyclopentyl]thioxomethyl]-4-nitro-L-phenylalanine methyl ester (460 mg, 44%; 65% based on recovered starting material) as a light yellow oil. HR MS: Obs. mass, 478.2014. Calcd. mass, 478.2012 (M−H).

Workup

  1. filtrationThe reaction mixture was filtered through a sintered glass funnel
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the crude product by silica gel flash column chromatography (hexane-ethyl acetate, 6:1

Sources & evidence

ORD record
ord-744bc78203964dedb4ee6ecfdcc1a0be
Source dataset
uspto-grants-2002_11
Patent number
US06479666B2

Reaction notes

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