p-Toluenesulfonic acid monohydrate → HCID 11198244, compound

HRID 1986519Notes

Reaction equation

HRID 1986519 reaction equation
[C:1]([O:4][C@H:5]1[CH:22]=[CH:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]32OCC[O:24]3)[CH2:6]1)(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[C:1]([O:4][C@H:5]1[CH:22]=[CH:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 9929412HCID 9929412, compound

Product 1

HCID 11198244HCID 11198244, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Ketal 5 (0.44 g) from Example 1 was dissolved in acetone-water (30 ml, 8:2), and treated with toluene-p-sulfonic acid monohydrate (0.1 g). After the mixture had been stirred at room temperature for 16 hr it was concentrated to half of its volume and diluted with a cold half saturated sodium bicarbonate solution. The solution was cooled, filtered to give white solid compound (0.38 g, 98%), which was further crystallized from methanol. M.p. 185-87° C., purity 99% (LC-MS).

Workup

  1. concentrationwas concentrated to half of its volume
  2. additiondiluted with a cold half saturated sodium bicarbonate solution
  3. temperatureThe solution was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-629aebaa6fa44ddcbd353aea2dda677b
Source dataset
uspto-grants-2009_06
Patent number
US07550450B2

Reaction notes

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