Benzyl [2,2-dimethyl-5-(prop-2-yn-1-ylcarbamoyl)-1,3-dioxan-5-yl]carbamate → Benzyl [2,2-dimethyl-5-(5-methyl-1,3-oxazol-2-yl)-1,3-dioxan-5-yl]carbamate

HRID 923486Notes

Reaction equation

HRID 923486 reaction equation
[CH3:1][C:2]1([CH3:25])[O:7][CH2:6][C:5]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:8](=[O:13])[NH:9][CH2:10][C:11]#[CH:12])[CH2:4][O:3]1>ClCCl.[Au](Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:25])[O:3][CH2:4][C:5]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:8]2[O:13][C:11]([CH3:12])=[CH:10][N:9]=2)[CH2:6][O:7]1

Participants

4

Reactant 1

HCID 131734990Benzyl [2,2-dimethyl-5-(prop-2-yn-1-ylcarbamoyl)-1,3-dioxan-5-yl]carbamate

Product 1

HCID 131734989Benzyl [2,2-dimethyl-5-(5-methyl-1,3-oxazol-2-yl)-1,3-dioxan-5-yl]carbamateYield 8.8%

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a solution of 400 mg of benzyl [2,2-dimethyl-5-(prop-2-yn-1-ylcarbamoyl)-1,3-dioxan-5-yl]carbamate in 4 ml of dichloromethane was added 104 mg of gold (III) chloride, followed by stirring at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 35 mg of benzyl [2,2-dimethyl-5-(5-methyl-1,3-oxazol-2-yl)-1,3-dioxan-5-yl]carbamate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3efb770032445e8b49e11aca197b9cf
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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