p-Toluenesulfonic acid monohydrate → HCID 86612133, compound

HRID 1162310Notes

Reaction equation

HRID 1162310 reaction equation
[CH3:1][O:2][C:3]([CH:6]1[CH2:10][O:9]C(C)(C)[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:5])[CH3:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:9][CH2:10][CH:6]([NH:7][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:3]([O:2][CH3:1])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 23138231Tert-butyl 4-(1-methoxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 86612133HCID 86612133, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(1-methoxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (2.5 g) obtained in Example 73a) was dissolved in methanol (45 ml), p-toluenesulfonic acid monohydrate (0.18 g) was added thereto, and mixed at room temperature for 20 minutes. The solvent was distilled off under reduced pressure, and the residue was diluted with ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a colorless solid (2.1 g, 95%).

Workup

  1. additionmixed at room temperature for 20 minutes
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b1926e87430e40ffae6ceeffc6bc2fa6
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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