Acetic Anhydride → HCID 118308722, compound

HRID 923495Notes

Reaction equation

HRID 923495 reaction equation
[OH:1][N:2]=[C:3]([C:5]1([CH3:19])[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[NH2:4].[C:20](OC(=O)C)(=O)[CH3:21]>ClCCl>[CH3:10][C:7]1([CH3:11])[N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:5]([CH3:19])([C:3]2[N:4]=[C:20]([CH3:21])[O:1][N:2]=2)[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131734993HCID 131734993, compound

Product 1

HCID 118308722HCID 118308722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 146 mg of tert-butyl 4-(N′-hydroxycarbamimidoyl)-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate in 4 ml of dichloromethane was added 55 μl of acetic anhydride, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and to the obtained residue were added 4 ml of DMF, followed by stirring at 110° C. for 15 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 113 mg of tert-butyl 2,2,4-trimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-oxazolidine-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the obtained residue were added 4 ml of DMF
  3. stirringby stirring at 110° C. for 15 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-923dfcf376d94d5e9f015b0ede2dc92a
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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