Dimethyl Sulfate → HCID 67304650, compound

HRID 1009745Notes

Reaction equation

HRID 1009745 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]([O:15][C:16]([NH:18][C:19]1[CH:23]=[C:22]([CH3:24])[O:21][N:20]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].S(OC)(O[CH3:29])(=O)=O>C1COCC1>[C:11]([O:15][C:16]([N:18]([C:19]1[CH:23]=[C:22]([CH3:24])[O:21][N:20]=1)[CH3:29])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11052591tert-Butyl (5-methyl-1,2-oxazol-3-yl)carbamateHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 67304650HCID 67304650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

Under an atmosphere of argon, a 1M solution of lithium hexamethyldisilazane in THF (1.1 ml) was added dropwise to a stirred solution of 3-tert-butoxycarbonylamino-5-methylisoxazole (Tet. Lett., 1996, 37, 3339-3342; 0.2 g) in THF (9 ml) that had been cooled to −5° C. After 10 minutes, a solution of dimethyl sulphate (0.1 ml) in THF (1 ml) was added dropwise and the resultant mixture was stirred at −5° C. for 2 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic phase was dried over magnesium sulphate and evaporated to give 3-(N-tert-butoxycarbonyl-N-methylamino)-5-methylisoxazole (0.19 g); 1H NMR: (CDCl3) 1.54 (s, 9H), 2.36 (s, 3H), 3.34 (s, 3H), 6.5 (br s, 1H).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-3244dc4d474f4982bd527ab895cdec23
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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