Lawesson's reagent → HCID 86587201, compound

HRID 478911Notes

Reaction equation

HRID 478911 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:16][NH:17][C:18]([C:20]2[CH:29]=[CH:28][C:23]3[NH:24][C:25](=[O:27])[O:26][C:22]=3[CH:21]=2)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:47])=CC=1>O1CCOCC1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:16][NH:17][C:18]([C:20]2[CH:29]=[CH:28][C:23]3[NH:24][C:25](=[O:27])[O:26][C:22]=3[CH:21]=2)=[S:47])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86587202HCID 86587202, compound

Product 1

HCID 86587201HCID 86587201, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide (686 mg, 1.31 mmol) and Lawesson's reagent (530 mg, 1.31 mmol) in dioxane (5 mL) were heated under reflux conditions for 2 hours. The solvent was removed, and the product was purified by chromatography (silica gel, 0-50% EtOAc in heptane) to give 2-oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide (559 mg, 79%): as a green gum:

Workup

  1. customThe solvent was removed
  2. customthe product was purified by chromatography (silica gel, 0-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-1a230d812bf94c3280085ba0b8c93da7
Source dataset
uspto-grants-2003_11
Patent number
US06642256B2

Reaction notes

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