Lawesson's reagent → HCID 59722608, compound

HRID 1664822Notes

Reaction equation

HRID 1664822 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH:23]1([C@H:29]2[CH2:35][NH:34][C:33](=O)[C@H:32]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[CH:23]1([C@H:29]2[CH2:35][NH:34][C:33](=[S:10])[C@H:32]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86620122HCID 86620122, compound

Product 1

HCID 59722608HCID 59722608, compoundYield 115.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Lawesson's reagent [2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (140 mg, 0.35 mmol) was added to a suspension of tert-butyl [(3R,6S)-6-cyclohexyl-2-oxoazepan-3-yl]carbamate (210 mg, 0.68 mmol) in toluene (8 mL) and the mixture was heated to 90° C. After 1 h, the reaction was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/ethyl acetate) gave the title compound (132 mg). MS 327.2 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-ef3730cd4e7f4fdf8996b7a25528ee8a
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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